Strange Bedfellows
by StartWhereYouAreUseWhatYouHave
Summary: An AU version of Jess' time in NYC when he returned from California in which Jess and Dean become friends.
1. Chapter 1 - Jess Ponders

**Chapter 1 Notes:** Trying out a new story idea. Please let me know if there is any interest in continuing with this concept. Sorry, the notes are so vague, but I don't want to give away too much of the story before you read the first chapter! Thanks for reading, and all reviews and thoughts are warmly welcomed.

 **Disclaimer:** I own nothing except my own obsession with Gilmore Girls.

 **Trigger Warning:** This story will feature homelessness. Also, this chapter contains two deaths of minor characters. The deaths occur 'off-camera,' but will be mourned by a main character throughout the story.

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Jess let himself into his tiny studio apartment and dropped his bag. He took off his hat, his jacket and his gloves leaving them in a pile by the door, his mind still processing what he had just seen. He had been walking home from his job at Kinko's, head down against the bitter cold, when he had glanced up and spotted a familiar figure turning from a side street and joining the flow of pedestrian traffic on the sidewalk a few feet in front of him. He had been instantly transported back to Stars Hollow, his heart pounding with the beginning of a fight or flight response. He had kept a reasonable distance between them as he followed, his eyes glued to their mark. About two blocks from his apartment, Jess had watched the figure stop and join the long line of men that formed outside St. Sebastian's every night. Jess had stopped short in surprise and had promptly been bumped by someone from behind. He had barely registered the, "Watch what you're doing, asshole!" hurled his way, the New York City version of excuse me. The moment had felt surreal. Jess had needed to confirm what he had seen. He had resumed walking, but at a slower pace, and sent a furtive glance toward the line of men as he lowered his head and made his way past. He had been right. It was definitely him. But, it made no sense. What the hell was Dean Forrester doing waiting in line at a homeless shelter in New York City of all places?

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Jess couldn't stop thinking about Dean as he heated up chili on the stove top for dinner. He decided he would call Luke after he ate to see if he knew anything about what was going on with Dean. But, first things first. He was starving. He removed the pot from the flame and poured the contents into a bowl. He stood at the counter, spooning the steaming chili into his mouth and thinking. After he was done with dinner and had washed his bowl and pot, he retrieved his cell phone from his jacket pocket and dialed the person he called the most. His uncle picked up on the second ring.

"Hey, Jess! I'm glad you called."

"Hey, Luke. Is now an ok time? Do you have a few minutes?"

"For you? Always. Just give me one minute. I'm going to step into the storage room so I can hear you better." Jess heard Luke call to Caesar that he'll be back in a few minutes, and it dawned on him that the dinner rush would still be going on at the diner. He probably should have waited another hour before he called. "Ok, I'm good now."

Jess smirked. "I thought there was a strict no cell phone policy in the diner. I'd hate to see you get in trouble at work. From what I remember, the boss is a real hardass."

Luke laughed. "He still is, but he's got a soft spot for when his favorite nephew calls."

"Aww, it's nice to know I get special treatment."

"How are you, Jess? Is everything ok?" They normally spoke every week, but almost always on Sunday nights. The few calls Luke had received from Jess on weeknights since the boy had moved to New York were usually indicative that something was wrong or that Jess was especially lonely and feeling down.

"Yeah. Yeah, Luke. I'm good." Now that Jess had his uncle on the phone, he wasn't sure how to ask what he wanted to know without it sounding weird.

"Good, I'm glad to hear it. So, what's up? Just missed me?"

"Actually, I was, uh, just calling to ask you something. It might sound strange, but what do you know about what Dean is up to these days?"

"Dean? Dean Forrester?" Jess could hear the surprise in Luke's voice.

"That's the one."

"Dean, your old high school nemesis? That Dean?"

"The very same."

"Why are you asking about Dean?" Luke's voice became more serious. "Did you hear about his family?"

"What do you mean? I haven't heard anything. That's why I'm asking."

"But, what brought this up? Why are you asking me about Dean now?"

"I think I might have seen him today. In New York. But, I'm not sure. I was just wondering if it really could have been him, or if he's still accounted for as a resident of Stars Hollow."

Luke paused. "It probably was Dean that you saw. He moved to New York. About a week after he graduated high school, his parents were in a car accident in Hartford. They got hit by a drunk driver, and neither of them made it. Dean and his little sister went to live with their aunt and uncle in New York. Dean had gotten into a college in Connecticut, but he was going to try to transfer to somewhere in New York so that he could be with his sister. It's very sad. I didn't know his parents very well, but they seemed like nice people. And, with his little sister being so young still… It was a real tragedy."

"Huh. That sucks."

"Yes, it certainly does suck, nephew."

"How come you never told me about it?"

"I don't know. You were in California when it happened. We weren't really talking at the time. By the time you came back and we reconnected, I guess it just didn't come up."

"Huh."

"If you run into him again, be nice. I'm sure he could use a friend right about now."

"We were never friends, Luke." Jess was surprised to hear the defensiveness in his own voice.

"I know that. I'm just saying, if you see him again, keep in mind what he's going through and be nice anyway. He might not have a lot of friends in New York yet, and he might appreciate seeing a familiar face. Maybe, without Rory to fight over, you guys can get past your high school crap and get along. That's all I'm saying."

Jess sighed. He wasn't sure why he wasn't telling Luke about the shelter. It somehow seemed too personal to talk about without knowing whether Dean was ok with people knowing about his situation.

"How are you doing otherwise, Jess? You staying warm?"

"Yeah. I'm trying. It's been brutal lately."

"Well, it's only going to get worse. I saw on the news this morning that New York is expecting temperatures in the single digits for the next week and a half. It's supposed to set a record for coldest January on the books. We're supposed to fare a little better over here with some days getting into the mid to high teens."

"Jeez, another week and a half of this shit? I should have stayed in freakin' California." Jess went through the motions of complaining about the weather, but his mind had already gone back to Dean, wondering what he did all day and how he kept himself warm when he wasn't in the shelter.

Luke chuckled. "Well, I for one am glad you didn't. You good, though? You still got all those blankets and quilts and everything? Your heat is working? You need anything?"

"I'm good, Luke. Yeah, I still have the blankets you gave me. The heat is working fine."

"And, you're using it right? You have the heat on enough to be comfortable?" Luke knew that Jess struggled with money and didn't turn the heat as high as Luke would like him to because of the cost. Luke worried about that, and about Jess' living situation in general.

"Yeah, I have the heat on. I'm fine."

"I don't know if you've been following the news, but there's a particularly nasty flu epidemic going around this year."

"The flu is a virus, Luke. You don't get it from being cold. Or having wet hair. Those are old wives' tales."

"I know that, smart guy. But, being cold lowers your body's natural resistance and makes you more susceptible to picking up the virus and getting sick. And, several otherwise healthy adults have died from the flu already this winter. It's really serious this year, and I just want to make sure you're taking care of yourself." Luke paused. "You're not here for me to check up on anymore, so I need you to tell me that you're taking care of yourself."

Jess softened at his uncle's concern. "I'm taking care of myself, Luke. I promise. I have the heat set to a reasonable temperature, I'm eating lots of soup and chili, and I go to sleep at night in the flannel pajamas you gave me for Christmas while wrapped in a comfy and cozy nest of the quilts that your mom made. You don't need to worry about me. I'm good."

Jess could hear the smile in his uncle's response. "Glad to hear it. And if you need anything, help with a heating bill, or anything, you'll let me know, right?"

"Yes, Luke. I will. But, right now, I really am ok."

"All right. I want to go out there soon to check out your new apartment and take you to lunch. When is good for you?"

"I'm not sure. I'll check my work schedule tomorrow and text you."

"Ok, Jess, sounds good."

"I'll let you get back to work now."

"All right, Jess. It was good talking to you. It's always good to hear your voice."

"Same here. 'Bye, Luke."

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After getting off the phone with Luke, Jess tried to settle down and read a book, but he couldn't focus. His mind kept wandering back to Dean. Jess wondered if he had misread what he had seen entirely. He really didn't know what Dean's situation was. Maybe he was making too many assumptions. It was possible the guy really was living with his aunt and uncle and was only volunteering at the shelter because he was the kind of kiss-ass do-gooder who did stuff like that. Maybe even for school credit or something. That thought brought Jess a measure of relief. But, his mind still wouldn't let him rest. Wouldn't the shelter have a separate entrance for volunteers? Or, wouldn't the volunteers be allowed in early to prepare the food instead of lining up outside in the cold with the shelter clientele? And, he hadn't liked the way Dean looked. His general level of dishevelment. Hair longer than he had seen him wear it before. Scruffy facial hair. Dirty, stuffed backpack on his shoulder. Head down against the cold and the wind as he walked. Eyes downcast in front of him as he stood in line waiting for shelter. He had had a hopeless look that had felt familiar to Jess. It called to mind his own brief period of homelessness, when he had run off to California after Luke had told him he needed to leave if he wouldn't go back to school only to find that he hadn't really been welcome in California either. He hated thinking about that period of his life, and he knew he would end up depressed if he let his mind linger on that time for too long. Jess sighed and put down his book. He put on his headphones, blasted whatever was in his CD player and tried to empty his mind and go to sleep. On nights like these, he really wished he could afford a television for distraction.

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After checking his work schedule at Kinko's, Jess had made a plan to get together with Luke. His uncle was going to come out to New York a week from Sunday. Jess was looking forward to seeing Luke, but once the date was set, he found himself surveying his tiny apartment, trying to see it through Luke's eyes. He took in the twin mattress on the floor. The two plastic storage containers with pull out drawers, one full of clothes and one of books and CD's. The foot and a half of counter space above the mini-fridge in the kitchen area. The stovetop with two small electric burners, but no oven. The narrowest shower he had ever been in. And the one very dirty window. He sighed. At least he could clean the window. Jess knew that this apartment was a great find, but he didn't think Luke would see it that way, and he didn't want his uncle to worry about him, or worse, pity him. He wanted Luke to see him as an adult, capable of living on his own and taking care of himself. Jess lived in a very small, studio apartment that was owned by a co-worker's family. It was originally a room in the family's apartment that they had walled off to create a rental space for extra income. They had added a tiny bathroom and an exit to the hallway, but in the end, it hadn't passed the size requirements stipulated in the zoning laws to qualify as a rental unit. It might be smaller than a standard studio apartment, but the upshot of this construction blunder for Jess was that the family was only able to rent it out on a cash basis to people they knew and trusted not to report them, greatly reducing the competition for the apartment as well as the price. The downside was that Jess had no official lease for the apartment. Luke had been skeptical when Jess explained the situation, worried about what Jess was getting himself into by renting from a landlord who couldn't even manage to set up a rental until correctly. Luke had relaxed a little when Jess had assured him that the room had its own entrance to the hallway as well as a second means of egress in the form of a fire escape off the apartment's only window. When he had first moved back to New York, Jess had originally moved into a much larger one room apartment with a friend and two other guys. He had always been aware that he required a lot of alone time, but he hadn't expected living with roommates to be so trying for him. He had chocked it up as a necessary evil to be able to afford to live in the city, and in the warmer months, when he could spend hours outside on his days off reading or people watching, it hadn't been so bad. When summer turned into autumn and then winter, Jess had started spending his free time at the library to avoid being in his cramped apartment, where it often felt too loud to think, never mind read or write. When his co-worker had told him about his parents' mini-studio and that their current tenant was moving out, Jess had jumped on the opportunity. He was paying more now than he had at his last place, but by a small enough margin to make it feel worthwhile. He loved having his own space. When he had to scrimp on costs in other areas, like food and heat, he reminded himself that coming home to solitude every night was priceless.

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Jess learned that St. Sebastian's shelter opened its doors at seven o'clock every night. He normally finished his shift at Kinkos at six o'clock and had a twenty-minute walk back to his neighborhood. In the evenings after seeing Dean, Jess found himself incorporating something new into his routine as he began to slow his pace in front of the shelter and take notice of the line of men that he had barely given a passing thought to prior to this week. Most evenings, he examined the line with discreet, sidelong glances, not wanting to stare or catch anyone's eye as he moved through the cold. The men seemed to cluster together in a bunched-up line against the side of the building, probably for warmth, often making it difficult to distinguish individual forms in the dark. One evening a few days after his first sighting, Jess spotted Dean in line. Even with his shoulders slouched and his head down, Dean still stood out as he loomed a half a head above the men standing closest to him. Jess stopped in his tracks, feeling panicked and conflicted. He and Dean weren't friends, not by a long shot. He can still remember Dean sucker punching him at Kyle's party and the fight that ensued. He can still remember the intense feelings of hatred he harbored every time he saw the other boy with Rory or had to witness the smug smile on his face when he felt that he had one-upped Jess in some way, but he no longer actually felt the anger and hatred, he just held the memory of it. He felt like he should do something, but he wasn't sure what. Did he really have some kind of responsibility toward Dean just because they had both lived in the same town, however briefly? Dated the same girl, gone to the same school, aggravated the shit out of each other? It wasn't a solid connection. He had no positive connotations associated with Dean. But, he couldn't deny that he knew him. Had sat behind him in English class. Bought batteries from him at the market. Met his little sister at the winter carnival. It was a connection, in a city full of transient passersby and anonymous interactions. Would Dean even want to see him? Or accept his help? What did Jess even have to offer him, anyway? He was probably the last person Dean would want seeing him like this. Jess pulled his hat down lower over his ears and continued his walk home. Laying in his bed that night, he couldn't sleep. He kept thinking about Dean and how desperate he must feel to be seeking refuge in a shelter. Maybe Jess was wrong about how Dean would react to him. He wondered what happened with the aunt and uncle and where Clara was. He snuggled into his warm bed, grateful to have this tiny room to go to every night and a warm, relatively safe place to sleep. He wondered what it was like in the shelter. What the conditions were like. And the other people. Whether Dean felt safe or scared. If he could sleep.

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One day the following week, Jess got stuck at work an extra hour because a co-worker had gone home sick. The weather still felt punishing and Jess was miserable on his walk home, cold, tired and hungry. He looked toward the shelter out of habit. No line. It was around twenty past seven so he assumed everyone must already be inside. He walked on, trying not to think about it. A half a block later, he spotted a recognizable figure moving in the dark, a few feet inside an alley, digging through a dumpster, pulling out what looked like a large piece of cardboard. Jess stood as if frozen in place, watching Dean dig through the trash, wondering why he wasn't in the shelter. Jess watched as Dean added the cardboard to a stack on the ground and then squatted down in front of it. He propped a couple of layers of cardboard against the wall and slid the rest near the wall on the ground, making a little cardboard chair. He lowered a gloved hand to the cardboard on the ground as if testing it for something, then he turned and sat in his makeshift cardboard chair. He pulled his backpack against his side and weaving one arm through the shoulder strap, wrapped his arms around the tops of his raised knees and lowered his head. The night was unusually quiet for this neighborhood, but Jess still couldn't be sure if it was his imagination or if he had really made out a small sniffle and a quiet sob. He watched as Dean's shoulders started to shake, knowing he wasn't imagining that, and he snapped out of his shock. He knew he needed to do something now. He could no longer convince himself that this wasn't his business. Dean could die out here tonight. Certainly, it was worth some potentially awkward conversation to keep that from happening. He thought about what Luke would do in this situation. And what Luke would want him to do. He took a deep breath and headed into the alley.

 **Author Notes:**

Right now, I am thinking this story will take place mainly in NYC and mostly focus on Jess and Dean. I already have a couple of ideas that will bring Luke to the city to check on the boys, but he won't be as front and center of a character as he usually is in my stories. Please let me know if there is interest in this story idea. All feedback is welcome and appreciated. Thank you.


	2. Chapter 2 - Jess Does Something

**Chapter 2 Notes:** More detailed notes are at the end of the chapter, because I didn't want to give away too much here. Thank you to everyone who took the time to leave me a review for the first chapter. It's always nice to hear from you, TheDisneyOutsider, my most loyal reader! :) All reviews and feedback are welcome and much appreciated.

 **Disclaimer:** I own nothing except my own obsession with Gilmore Girls.

 **Trigger Warning:** Homelessness. Suicidal thoughts.

Jess walked quickly into the alley, trying to exude more confidence than he felt. He knew he needed to get this over with before he had time to change his mind. It wasn't until he was almost in front of Dean that he realized he had failed to prepare a conversation opener. Dean looked up with a start, fear clear on his face. For a split second, Jess felt a spike of defensive anger, feeling the look was directed at him on a personal level, as if Dean believed Jess had come to kick him while he was down. Then it hit him that all Dean could see in the dark was a stranger suddenly looming over him in an alley. Dean hurried to get his feet under him and grabbed his backpack. Jess rushed to explain himself before Dean ran off.

"Dean, stop! It's me, Jess!" Dean froze in a half-crouched position, looking up at Jess in shock.

"Jess Mariano." Jess paused for a response, but when Dean continued to stare at him in disbelief, Jess couldn't stop himself from filling the silence. He had expected their exchange to be awkward and maybe even hostile, given their past dynamics, but he hadn't expected to feel this nervous. He stuffed his gloved hands into his pockets for something to do and plunged on. "C'mon, man, you must remember me. I stole your girl. You tried to kill me at a high school party. Any of this ringing any bells for you? Cause, if not, I have to say, I'm a little hurt. Clearly our relationship meant more to me than it did to you."

"Jess? Really?"

"In the flesh. Very cold flesh, I might add. As much fun as I'm having catching up with you in this cold, dark alley, I think we'd both be more comfortable if we head over to my place. I'm only about a block and a half away. I can make us dinner. And we can make up for all the swell slumber parties we hated each other too much to have in high school. What do you say? Get warm, then catch up?" Jess sighed inwardly at his inability to turn off his sarcasm and just shut his damn mouth. He had pictured himself approaching Dean as an earnest hero, all solemn concern and empathy, not as a smart-ass with verbal diarrhea. No wonder Dean wasn't excited to see him. He must have thought Jess hadn't changed at all since high school.

Dean stood all the way up to face Jess, his expression a combination of embarrassment and disbelief, tinged with a tiny flicker of hope. "Are you serious, Jess? Please…" his voice cracked slightly and he looked down for a moment before regaining eye contact. "Don't just mess with me…..."

"Dean, you wound me." Jess lowered his voice and spoke honestly, without artifice. "C'mon, man, I'm not that much of a jackass." He paused. "Now, can we please go? I'm freezing my balls off out here."

Dean nodded and followed Jess out of the alley. They walked side by side in silence until they got to Jess' building. Jess unlocked the security door as quickly as he could with clumsy fingers that were starting to lose feeling even in gloves. He thought about Dean hunkering down to spend the night with no protection from the cold and the idea made him queasy. He led Dean up a flight of stairs and then into his unit. He quickly walked over to the thermostat and turned the heat up. "It'll take a little while to get warm in here, but, if you want to warm up faster, you're welcome to take a hot shower while I make dinner."

Dean exhaled, staring at the apartment, and when he spoke his voice was barely above a hoarse whisper. "A hot shower would be amazing."

Jess tilted his head toward the bathroom while he took off his jacket and unwound his scarf. "Ok, it's right through there. There's shampoo and soap and stuff, so help yourself to whatever you need."

Dean looked at Jess then and cleared his throat. "Thank you, Jess. Really, just thank you." His voice cracked on the last word, and he felt dangerously and ridiculously close to tears.

Jess just nodded. "Ok, I'm going to start dinner. You good with chicken soup and a tuna sandwich?"

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Dean stood under the spray of the shower, soaking in the warmth of the hot water. He felt grateful. More grateful than he'd ever been for anything in his life. He started getting the feeling back in his fingers, his toes. It felt amazing to be able to savor a shower again, without having to worry about his physical safety or about keeping an eye on his meager worldly possessions. It felt almost decadent to be able to shampoo his hair a second time, before rinsing himself clean. As much as he would have loved to stay in the shower longer, he didn't want to run the risk of using up all the hot water and overstaying his welcome in the first few minutes of being at Jess' place.

He turned off the shower and quickly dried himself off with the towel from his backpack. It was starting to smell like mildew again. He never really got the chance to let it air dry after using it, so it usually ended up getting gross quickly. And then tainting everything else in his bag with a rotten, moldy smell. He pulled on a pair of sweats. He had been trying to keep to a system, rotating his two pairs of pants so that he wore the jeans outside for warmth and the sweats inside the shelter as pajamas. The system had broken down last week when he had slipped on an icy patch in the park and had landed ass first in a wet snowbank, soaking his jeans through to his skin. He had spent the next few minutes in real pain from a cold so intense that it felt like he was burning until he had been able to find a public bathroom where he could strip his jeans off, dry his legs with paper towels and change into his sweats. He thought about his laundry situation as he pulled on a pair of dry, if not clean, socks. He really needed to go to the laundry mat tomorrow. That thought brought Dean's mind back to his dwindling financial resources, and he tried to shake the thought loose before his usual panic could set in.

He pulled a thermal tee shirt over his head and then a sweatshirt. He sighed and looked in the mirror. He looked like hell. He felt even worse. He needed to get himself together. He could feel so many emotions bubbling up right under the surface. Tonight, he knew, had been the new low point in his life. He had huddled in that alley not knowing if he was going to make it through the night. He knew there were options other than sleeping outdoors on a night like tonight. There were all night diners to kill time in. Twenty-four seven convenience stores. All night movie theaters. This was New York, with more all night options than you could shake a stick at. He knew that. But, tonight. Tonight, he had had it. When he had missed the cut-off to get into the shelter, a deep-down part of him had wanted to just give up. To curl up in a ball and die. He couldn't deal with his life anymore. Everything had gotten too hard, and he couldn't take it. He wasn't strong enough. Tonight, he had really thought about opting out of the despair and abject loneliness that had been his life for the past two months. He wouldn't even have had to do anything. He could have committed suicide passively, by letting the cold take care of it for him. Just drift off to sleep and never wake up. He was disgusted with himself now for his cowardice, and for how close he had come to abandoning Clara. She had been through enough without losing him, too. What kind of big brother would let himself die when it would crush his little sister, a twelve-year-old girl who had lost both her parents less than a year ago? A weak, selfish asshole, that's who. His aunt and uncle were right. He was a terrible person who only cared about himself. No wonder they had thrown him out.

But now, now he had been rescued by the unlikeliest of heroes. He felt tears welling in his eyes for the second time that night. This time from relief for the kindness that he knew he didn't deserve. He had been terrible to Jess in high school. And now he had to face up to his shitty past behavior along with everything else he was dealing with. He didn't want to cry in front of Jess and make this night any more uncomfortable than it had to be. He needed to stop before he went back out there. He ripped off a short length of toilet paper, no more than he thought he would need having a new respect for rationing resources, balled it up and wiped at his eyes. He needed to get his shit together. This was a second chance. If nothing else was certain, he at least knew he was going to make it through the night now. And, for the moment, at least, he wasn't completely alone. Not really. That was something. That was huge.

Dean stepped out of the the bathroom to find Jess pouring soup from a sauce pan into two bowls on the counter. He looked at Dean and forced a small smile onto his face. "So, uh, I usually just eat standing at the counter, or sometimes sitting on the floor, but that's kind of tricky with soup and a sandwich. But, you're welcome to do whatever you want. Here's yours." He pushed one plate and bowl about a foot down the counter from his own to give Dean, and himself, some space.

Dean wasn't sure how to act. Part of him wanted to hug Jess, as crazy as that instinct seemed, to show his thanks, but also for the selfish reason of wanting physical contact from the first safe person he'd encountered in a long time. He had always been a tactile person, and it had been way too long since someone had comforted him with a hug, or any kind of touch. He wasn't sure how it would go over, though, so he limited himself to a verbal response. "Thanks, Jess. Really, I can't thank you enough for this. I really appreciate you letting me stay here tonight. You have no idea."

Jess smiled again, and it felt less forced this time. "It's ok, Dean. So, are you just going to stand there, or are you going to eat?"

Dean huffed out a soft laugh and walked over to his dinner. The counter wasn't very long, and he and Jess were standing almost shoulder to shoulder as they ate. Dean didn't mind. He was enjoying being in close proximity to someone without having to fear for his safety. He ate spoonful after spoonful of the chicken noodle soup in silence, savoring the feeling of warmth spreading inside him as well as the flavor. He was about to move on to his sandwich when Jess broke the quiet. "So, uh, I guess you'll have to sleep on the floor. But I have a bunch of quilts and blankets. They're pretty thick and really warm. You can fold one up and lay on it and then put a couple over you. I did that for a while at my last place, before I was able to buy the mattress. It wasn't ideal, but it was ok. I think you'll be warm enough, and hopefully not too uncomfortable."

"That sounds great, Jess. Honestly. I'm just grateful to be indoors. Warm. And dry. Really. Thank you."

Jess nodded. "So, uh…" Jess wanted to know what had happened between Dean moving in with his aunt and uncle and Dean sleeping in homeless shelters, but he didn't know how to ask and didn't want to pry. "I'm really sorry about what happened with your parents."

Dean looked over at Jess in surprise.

"Oh, uh, Luke told me."

"Oh, right. Thank you. I don't really want to talk about it, though, if that's ok."

"Sure, of course. Sorry."

Dean tried to shake off the reference to his parents before the dark thoughts could take hold and the panic could set in. He steered the conversation to lighter territory. "So, uh, how is Luke doing anyway?"

"Luke? He's good. He's the same old Luke."

"Good. That's good. He's a good guy."

"Yeah, he is. He is a good guy." Jess wasn't particularly tired, but he was already starting to look forward to going to sleep to put this conversation out of its misery. He had expected this to be awkward, but he hadn't expected his verbal skills to completely abandon him like this.

"So, um, I kind of want to apologize. For, you know, everything in high school, and, uh, starting the fight at Kyle's party. I'm sorry for that. I was jealous, and it was stupid and childish of me. And I would take it back if I could."

It was Jess' turn to be surprised. That was the last thing he was expecting. "Uh, ok, thanks. I think I played a role in it, too, though. I mean, true, you did sucker punch me out of the blue at the party while I was innocently minding my own business and everything…" Jess paused to give Dean a chance to chuckle at his version of the narrative, but when he glanced Dean's way, he saw him nodding in solemn agreement, an embarrassed expression on his face. "But, I know I'd been pretty consistently pushing your buttons since I moved to town. I get why you wanted to take a swing at me, or you know, fifty of them." Jess paused again, deciding how much to give Dean, but then he figured what the hell. "I was unhappy, and angry, mostly at myself, but I took it out on you instead." Jess shrugged. "Because you were there, I guess. You had something I wanted." Jess knew Dean would assume he was referring only to Rory, and that was fine with him, because he wasn't ready to admit that he had been jealous of Dean in other ways, too. For his happy, normal family. His effortless likability. His comfort in his own skin. "And pissing you off was easier, and if I'm being totally honest, more fun, than dealing with my own shit. So, I'm sorry, too, for how I acted back then."

Dean smiled softly. "Thanks, Jess. I appreciate that. So, we're ok, then?"

Jess nodded. "I think so. We're good on my end."

"Ok." Dean grinned. "Mine, too. Thanks for that. And, seriously, Jess, thanks again for tonight. I mean it. You saved me tonight. I can't stop thanking you for this."

Jess smirked. "Well, we won't really know if that's true unless you try, now will we?"

Dean barked out a laugh. "Sorry, if I'm making you uncomfortable. I'm just really grateful."

"Really? I had no idea! You've been so stingy with your thanks."

Dean chuckled softly. "Ok, I get it. I'll try to stop." He was smiling as he started on his sandwich.

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Jess was lying on his mattress reading while surreptitiously watching Dean bed down for the night. He had given him two quilts and a blanket. That still left him with one quilt and one blanket for himself. One of the quilts and the blanket he had given Dean were truly surplus bedding that he usually kept folded up in one of the plastic storage units. He normally slept cocooned inside two quilts, but he figured he could make do with one. He wanted to make sure Dean was comfortable since he was the one sleeping on the floor. Luke's mother, Jess' grandmother, had been a skilled quilter, and Luke had outfitted him with three of the quilts she had made when he had first moved to New York. The other two blankets had come from Luke, as well. His uncle had been set on him not freezing to death this winter. He had seen it as excessive at the time, but they had come in handy for sleeping on at his last place and he was grateful to have them now to offer to Dean. He watched Dean fold up one of the quilts to sleep on, roll up the clean towel Jess had given him to use for a pillow, and tuck himself in under the blanket and the second quilt. The whole process involved so much squirming and adjusting that it reminded Jess of a cat settling into a spot for the night. "You all right over there?" Jess asked once Dean seemed to be settled in.

Dean sighed contently and smiled broadly. Being clean, fed and warm was making him feel more like himself than he had in while. "I'm great. Honestly. This is the most comfortable I've been in a long time. I feel like I'm going to sleep really well tonight. I would thank you again right about now, but I don't want to piss you off."

Jess returned the smile with a small one of his own. He was glad Dean was comfortable, but he really wanted to ask about the shelter. If Dean was this happy to sleep on the floor in his cramped little apartment, the conditions at the shelter must have been pretty bad. Jess wasn't sure where he should go with this situation. Part of him wanted to tell Dean that he didn't have to go back to the shelter. That he could stay with Jess until he got on his feet. Another part of him worried about making the offer and regretting it later. What if it took Dean a long time to get a job and a room somewhere? What if they drove each other nuts, or worse started antagonizing each other again once the bloom had worn off their shiny, new friendship? The whole purpose of Jess paying more rent than he could reasonably afford had been for the solitude. Was he honestly ready to give that up to help Dean? He needed to think about this more before he said anything to Dean. He wished he had a neutral friend to kick this idea around with, but he didn't really have any close friends right now. He knew he could talk to Luke, he could always talk to Luke, but he also knew what Luke would say. That helping Dean was the right thing to do. But, did that have to mean taking him in? Wouldn't it still be helping Dean if Jess met up with him every so often, maybe brought him food and toiletries or whatever else he needed? Maybe told him he was welcome to stay with him if he had another night when he couldn't get into the shelter? Jess knew on some level that that was a cop out, but he wasn't sure how much he wanted to give to a guy he barely knew and for most of their history together, hadn't liked. He knew that it would make sense in terms of karma. Jess would be paying forward what Luke had done for him. Putting a roof over the head of someone who needed one. And Luke hadn't known Jess very well when he had taken him in either. Sure, they had had a family connection, but they hadn't seen each other in years before Jess' arrival in Stars Hollow and Luke really hadn't known what he was getting himself into. But, he had taken Jess in anyway. Jess knew he wasn't going to reach a conclusion tonight. He needed to sleep on this before he did anything hasty.

"I'm probably going to keep the light on for a while and read. Do you want a book or anything? There's a bunch in the plastic container nearest you if you want to take a look."

Dean yawned. "Thanks, but I'm good. I'm pretty sure I'm going to pass out any second."

Jess just nodded, his mind still churning.

"Goodnight, Jess."

"Goodnight." Jess tried to focus on his book, but he could already tell the effort was pointless. He listened to Dean's breathing level off as he drifted off to sleep.

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Dean felt a hand on his shoulder, gently shaking him into consciousness. He just needed five more minutes of sleep, then he would get up for school. No problem. Just five more minutes. But, his mom was being very persistent this morning.

"Hey, c'mon, man." Dean startled awake at the voice that was too deep and too male to belong to his mother. His loss came flooding back to him once again, but there was no time to dwell on it as his fear instinct took over at being accosted at his most vulnerable. He jerked back from his would-be assailant, arms flailing, heart pounding in his chest. He didn't realize he had connected until he heard a soft "Ow, seriously." This time he recognized the voice. Everything came into focus and he found himself looking at Jess, who was kneeling a foot away on the floor, one hand rubbing the opposite shoulder, a small frown on his face.

"Oh, shit, Jess! I'm sorry! I didn't know it was you."

"Yeah, should I start wearing a nametag?"

"I'm so sorry, Jess! I forgot where I was. I was so out of it. I thought I was being attacked. I'm sorry." Dean could feel the tears coming and fought to hold them back. Had he fucked this up already? He didn't want to lose this new connection to Jess. Going back to being alone would be even harder now that he'd been given this brief glimpse of something normal. Now that he had been reminded of what being a person felt like.

Jess sighed. "It's ok, Dean. I'll live. I probably shouldn't have woken you up like that, anyway. I should have realized you'd be…jumpy."

Dean noticed that Jess was already dressed in jeans and a uniform polo shirt with the Kinkos logo on the left side of his chest. "Oh, man, do you need to leave for work? Can I just change into my jeans really quick before I go? It'll just take two seconds, I swear."

Dean sat up and started hurriedly rummaging through his backpack. He had figured Jess would wake him in time for him to shower before he had to leave. He had really wanted to get another shower. And to not feel so frantic. The disappointment hit him hard. He felt like he could vomit as he started to pull out his jeans. They were stuck on something and when he yanked, he heard the sharp sound of fabric ripping. He took the jeans all the way out and saw the zipper of the fly caught on a torn piece of his warmest shirt. Dean wanted to cry and he knew he wouldn't be able to hold off the tears much longer. He hoped he could at least hold off until he got away from Jess.

"Dean!"

When Dean focused back on Jess, he had the distinct impression that Jess had been saying his name for a while.

"Dean." Jess' voice was softer this time. "You don't have to go now. You can stay here today if you want. That's why I let you sleep in." Jess still didn't feel ready to commit to letting Dean stay with him indefinitely, but offering to let him stay for the day was something. It wasn't nothing.

"Seriously?"

"Yeah. I don't have a second key to give you and if you leave the door is going to lock behind you and you won't be able to get back in. But, if you want to stay in and catch up on your sleep, you can. I get out at six. There's food in the kitchen, mostly canned stuff, and some eggs in the fridge, but help yourself to whatever you want. Take another shower if you want. There's a CD player on my bed and CD's in that plastic container with the books. Feel free to entertain yourself. Ok?"

Dean nodded, his body finally relaxing. "Ok. Thanks, Jess."

"All right." Jess smiled and stood up. "I'll see you around six thirty then. Have a good day."

"I will, Jess, thanks. Have a good day at work."

Dean watched Jess let himself out of the apartment, and then laid back down, snuggling himself deeper into the blankets. As he predicted, last night had been his best night of sleep in a long time, but he still felt like he could sleep for days. And sleep, when he could get it, was always a safer option than letting himself think about his situation and worry about all the uncertainties running through his mind.

 **Author Notes:**

Though there was no Luke in this chapter, I'm thinking he will be more involved in the future through phone calls and visits. I wanted his only presence in this chapter to be the effect he's had on Jess, but I ultimately wanted the decision to help Dean to be made by Jess alone, with out external guidance.


	3. Chapter 3 - Dean Stays a While

**Chapter 3 Notes:** Had some issues posting this chapter. Apologies to anyone following the story who originally received a link to nowhere. Thank you to everyone who is reading my story and has taken the time to review the first two chapters. Your feedback is welcome and appreciated.

 **Disclaimer:** I own nothing except my own obsession with Gilmore Girls.

 **Trigger Warning:** Homelessness.

Jess' workday dragged even more than usual. He tried to keep his mind off Dean and his situation, but his job wasn't mentally engaging enough to provide a real distraction, and everything that happened kept leading him back to Dean in one way or another. Most of his day involved printing and putting together printed products. Today it had been presentation materials for a psychology lecture, corporate training manuals, pamphlets on STD prevention, and posters offering a reward for a missing cat for an older female customer. Her sadness had been palpable. Jess had used his employee discount when he rang her up and had wished her good luck. The polite smile she had given him when she thanked him hadn't reached her eyes. The woman's loss lingered in Jess' thoughts as he went about his repetitive tasks. In his imagining, she lived alone and had no family and her cat had been her main companion, and she was feeling the loss as acutely as a parent would for a child. Jess tried to shake the idea from his head, wondering when he had become so maudlin. He couldn't keep himself from comparing the cat's situation to Dean's, cold and scared, and lost and alone on the streets of New York. Jess was still debating how involved he should get with Dean's predicament. He still didn't know why Dean was no longer staying with his aunt and uncle. He wasn't sure if he could ask Dean about that before he decided to let him stay, or if it was too personal, or just plain rude. It wasn't really his business, but if Jess was going to take in a roommate, he wanted to know all the facts, especially related to why things didn't work out at his last place. That was just good sense.

A few hours into his shift, Jess had the bad luck of answering the phone when Omar had called to say he couldn't make it in to work for his shift. His pregnant wife had been mugged at knife point in the middle of the afternoon on her way to work. She had handed over her purse willingly, but her attacker had roughly pushed her down anyway before running off. They were waiting to see a doctor at the emergency room now to get the baby checked out. Jess heard Omar's voice catch at the mention of the baby. Jess offered his sympathy and relayed the message to their supervisor. Jess didn't think of himself as being a particularly sensitive person, but some days the world just seemed like too much to take, with all the suffering and loss. He knew that life wasn't fair. Had learned that important lesson as a very young boy living with Liz. But, somedays the harsh unfairness took more of a toll on him than others. He went back to running through the mechanics of his job trying to clear his mind. Before long, his thoughts were back on Dean, wondering if he had ever been attacked on the street, or in the shelter. And how he got in this situation to begin with, homeless and without money or support. That got Jess reflecting on his own precarious financial situation. He was scraping by month to month. The rent he paid to live by himself was more than he could reasonably afford on his salary, but he got by. Just barely. He didn't know how he was supposed to feed another person when he could barely feed himself. It had taken him a while to get more than just part-time work when he had moved to the city, so he knew it could take Dean a while to get something stable, too. He only had a few hundred dollars in his savings account at the moment, but he knew his real emergency fund lay in his family support. Luke would help him. He knew that. And he would need his uncle's help in order to help Dean. He knew that, too.

Jess clocked out for his lunch break. The television in the staff room was showing a news report about the plight of homeless people in New York in this brutal winter weather. A solemn faced woman bundled up in layers of outerwear reported into her microphone that in the past month, two homeless people had already died from exposure, one found on a park bench and one lying in the bushes. Temperatures were lingering in the single digits. Shelters were overflowing. Cops were making late night rounds trying to encourage the homeless people still outside to seek shelter in the high school gyms and other public buildings that had been turned into warming houses to aid the homeless through this dangerous cold spell. Jess felt his stomach twist. He saw the cat owner's sad smile. Heard the hitch in Omar's voice. He could feel bad for them, and he did, but he couldn't do anything for them. But, this right here. Dean being homeless. This, he could do something about. He stared at the rest of the news segment, knowing that this was being literally pushed right in his face for a reason. He didn't know if it was Luke's effect on him, or if living in Stars Hollow, with its small-town vibes and residents who cared about each other, had changed him, but he was caught off guard by the emotion of how much he suddenly wanted to help. To be a friend to Dean, and even more importantly, a good person in his own right. Someone with a connection to something bigger than himself, who added value to someone else's life. Someone who contributed something.

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Jess let himself into his apartment with butterflies in his stomach. A small part of him was worried that Dean would no longer be there, and that all his wrestling with the issue would have been for nothing. Now that he had made up his mind and become attached to the mental image of himself as a Good Samaritan, he was nervous about losing this opportunity to prove his mettle. He didn't need to worry, though, as Dean was lying on the quilts on the floor, a pensive frown on his face, reading Jess' copy of 'On the Road' when he walked in. Dean looked up and smiled at Jess.

"Jack Kerouac. Always a good choice." Jess started stripping off his jacket and winter accessories, piling them by the door.

"You like this guy, huh?"

"I own the book, don't I? That should tell you something." Jess pulled off his boots and set them by his pile of clothes.

"I'd always heard so much about this book, but now that I'm actually reading it, I don't know. I'm finding it pretty stressful."

"Stressful?"

"Yeah, like the pace. It feels so frenetic and…yeah, just stressful."

"I guess he's not for everyone." Jess tipped his head toward the plastic storage bin. "There's other stuff in there, you know. You don't need to read something you don't like."

"Yeah, I know. But, now that I've started this one, I guess I should finish it." Dean realized what he had said and he knew his face was registering his embarrassment. He wouldn't get the chance to finish the book. It's not like he was staying here. He needed to go before he put Jess in the uncomfortable position of having to ask him to leave. He tried to backtrack. "I mean, if it's ok if I borrow it. And take it with me. I'll get it back to you. I promise." Jess had a small, weird smile on his face. Dean suddenly felt like they were back in high school and Jess was about to make fun of him and verbally tear him down in some way for making such a stupid assumption. Dean got to his feet and started getting his things together. Time to go. "But, if you don't want me to borrow it, I get it. It's not that big a deal anyway. Like I said, I don't even like it that much. I feel like that guy needs Ritalin or something."

Jess knew he needed to speak, but he felt more uncomfortable than he thought he would. He was ready to do the right thing, here, but why did everything need to involve an awkward conversation?

"Dean, you don't have to go. I mean, you can keep staying here…If you want to."

Dean froze, his backpack dangling from his hand by one strap. "Really? Are you serious?"

"Yeah, I'm serious. I've been thinking about it all day. I'm sure."

"Really sure? I mean, you don't have a lot of room here and I don't want to be in your way."

"You're not in my way, Dean. If you want to stay, you're welcome to. It's up to you. I won't be offended if you don't want to."

"I definitely want to, Jess. This is the best place I've stayed since-" Dean caught himself. "In months. I just…...I don't want to be a drain on you. I can give you what I have left for money, which isn't much. Not much at all. But, I won't be able to kick in anything else until I can get a job, which I haven't had much luck with yet. And, trust me, I've been trying."

"I'm not asking you for money, Dean. But, maybe getting a job will be easier now. You can put my phone number and address on applications. That might help, right? They'll have a way to get in touch with you."

Dean felt his eyes getting wet. Dammit, he was turning into such a crier. "That would be amazing, Jess. I just…I don't want to take advantage of you. You've been so nice to me already. And, I don't know, you just, you don't owe me anything, you know. We weren't even friends before last night…"

Jess smirked. "Hey, slow your roll there, Forrester. Who says we're friends now?"

Dean barked out a laugh, still feeling on the verge of tears even as he smiled. Jess smiled back.

"I'm serious, though, Jess. Are you sure about this?"

Jess nodded. "I think I am, Dean. I know you're in a tough spot right now, and I want to help. I'd want someone to do the same for me if I was in your shoes. Plus, it hasn't been too terrible having you around. Now that we've spent some non-pugilistic time together, I have to say, you're actually not the worst guy in the world." Jess shrugged. "Who knew?"

Dean huffed out a soft laugh. "I get the impression that's almost a compliment, coming from you."

Jess smiled slightly, trying to look encouraging.

"Just so you know. You're not the worst guy in the world either, Jess."

"So, ok?" Jess prompted.

Dean nodded again. "Ok."

"So, you're staying?"

"Yeah, I guess I'm staying." Dean lowered his backpack to the floor. "Thanks, Jess. I really owe you for this. I'm going to start looking for a job again tomorrow. I don't want to be a freeloader. And, I'll pay you back for everything the second I have money coming in. I swear. Thank you so much. I can't even tell you how much I appreciate this."

Jess nodded, starting to feel uncomfortable in the face of Dean's thankfulness. "I'll get a second key made during my lunch break tomorrow. And don't feel like you need to start job hunting tomorrow since you won't be able to let yourself back in. I don't want you to get stuck out in the cold." Jess debated giving Dean his key, but something held him back. It was one thing to share his space with Dean, but it was another entirely to be dependent on Dean to let him into his own apartment at the end of the day.

Dean nodded. "Ok, then I'll start looking on Saturday. I promise. I'll get something soon."

Jess nodded. "Ok, now that all that's settled. What do we want for dinner?" He pulled open the cupboard and saw one can of tuna fish, a package of crackers, and two cans of soup. The bread usually lasted him until Saturday, when he hit the market on his way home from work to replenish his stock, but he had used the last slices on Dean's sandwich the night before. "How do soup and crackers sound to you?"

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The following day was Friday, which meant payday. Jess walked into the apartment feeling the same sense of relief and joy that payday always brought him, the relief at having once again made ends meet without running out of money, and the joy attributable to the illusion of having wiggle room in his budget that cash in his pocket always gave him. Jess entered the apartment excited to share the treats he had brought home, but his good mood faltered when he saw Dean, sitting on the floor, back against the wall, one leg out straight in front of him and one bent at the knee, looking completely wiped out.

Jess set what he was carrying on the counter and started taking off his outerwear.

"Hey, are you ok?"

As Dean nodded, the light reflected off his face and Jess could see that he had been crying. Jess opened his mouth to ask what was wrong before realizing how stupid a question that was. Everything was wrong. From where he was standing, it didn't look like Dean had anything in his life that wasn't wrong. He shut his mouth for a moment and tried again. "Is there anything I can do, Dean?"

Dean shook his head slowly. He wiped at his eyes with the back of his hand, embarrassment clear on his face. "I'm sorry, Jess. I'm sure you don't want to come home to this."

Jess couldn't agree more, but he wanted to say something comforting. And he did get it. Dean had been projecting a pretty positive mood for the past two days, so Jess was caught off guard tonight, but it made sense. With the state of his life being what it is, Jess was impressed that Dean didn't break down every day.

"Don't be sorry. I get it. I have days like that, too, and I'm not going through the stuff you are."

"I had…" "I had a panic attack. I started thinking about everything…about my life. And Clara. And my parents." Dean's voice caught. "And I just…I started panicking. I don't know how to deal with any of it….It passed, but I'm always really exhausted after."

"You want a glass of water or something?"

Dean nodded, running one hand through his long hair, trying to compose himself now that he was no longer alone. "I'll get it." He slowly got to his feet and walked toward the sink.

Jess remembered the things he had brought home and joined Dean at the counter. "Hey, you like Chinese? I picked up vegetable fried rice, sweet and sour chicken and beef teriyaki."

Dean looked at Jess in surprise. Picking up Chinese felt so normal, but also extravagantly out of place in either of their current situations. "Are you serious?"

"Payday." Jess said with a smile by way of explanation. He always picked up something on the way home on Fridays, but usually something cheaper, like a few tacos or fast food. He felt more justified in spending more tonight since he had a guest to feed.

"That sounds great, Jess." Dean took a small sip of his water, watching as Jess opened each container and set them on the counter. Dean breathed in the warm, salty smell and his stomach growled loudly in response.

Jess laughed, then looked at Dean seriously. "You did eat today, right?"

"Uh, yeah, I ate some stuff. I wasn't sure what you wanted to have for dinner, so I didn't want to accidentally eat something you were planning on having tonight."

Jess was getting out plates and forks. "What did you have to eat today?" He had a sudden memory of all the times Luke had asked him that very same question, and he mentally laughed at himself.

"Um, some crackers. And I found some peanut butter. I put a little of that on the crackers."

Jess nodded, feeling a twinge of guilt. He hadn't left Dean with much in the way of food in the apartment. He hadn't really thought about it this morning when he left for work. "I'm going to go grocery shopping after work tomorrow. I had a copy of the key made while I was out cashing my paycheck on my lunch break. Two copies actually, one for you and I figured I should make a spare while I was at it, just in case. So, you won't be stuck in the apartment when I'm at work tomorrow. It can't be fun sitting in here all day."

"Trust me, it's much better than sitting out there all day. It was a little boring, but I felt safe. And I was warm. And the morning was pretty good. I caught up on some sleep and took a shower. The afternoon was not so good, though. I tried to read more of 'On the Road,' but I couldn't get into it enough to really distract myself, I guess, so I got to thinking and…well, that never leads to anything good anymore."

Jess wondered when Dean had had the panic attack, and how long he had been sitting by himself crying when Jess had found him. "Oh, that reminds me." Jess dug into the second plastic bag he had been carrying and took out two magazines. "I brought you these. They order them for the break room at work, and these were about to get tossed because the new issues came in."

Dean took the offered magazines. Sports Illustrated and Motor Trend. "Thanks, Jess."

"I wasn't really sure if you were into those, but I seem to remember seeing you wear a team jersey or two back in high school. And I know you built that car you gave Rory. Which, uh, I'm sorry for wrecking by the way. So, I figured I'd see if you wanted them."

Dean chuckled, knowing he needed to keep talking, keep things light, and not get wrapped up in memories of all the evenings and weekend mornings that he had spent working side by side with his dad on that car for Rory. He was grateful to have the memory, but he couldn't take it out and look at it now, not without losing it in front of Jess. "I think you've more than made up for the car. And these are great, Jess." Dean lifted the hand holding the magazines. "I really appreciate you snagging them for me."

"No problem." Jess knew he needed to get something out before he lost his nerve. "And, Dean, if you ever want to, uh, talk about stuff, like anything, I guess, I'm around. And I'm a pretty decent listener."

"Thanks, Jess. I really appreciate that."

Jess nodded. "Ok, then, let's eat before it gets cold."

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"Hey Jess!" Luke answered the phone. "How's life in the big city?" The second non-Sunday night call from Jess in two weeks. And it was Saturday afternoon, so Luke knew something was up if Jess couldn't wait until the next day to talk to him.

"It's ok. How's life in Norman Rockwell's small-town America?" Jess wanted to give Luke his news. That Dean was homeless. That he was staying with Jess. He wanted to talk to Luke about his concerns about feeding two people. He knew he could count on Luke to help him, with the offer of a no strings attached gift rather than a loan. But, he couldn't get any of that out.

"The same as when you left. That's the beauty of living in a Normal Rockwell painting, my friend. There's rarely ever any real change." Luke chuckled briefly, before turning serious. "Is something up, Jess?" Jess could hear the concern in his uncle's voice.

"Not really."

"Well, I'm really looking forward to seeing you next Sunday."

"Me too."

"I want to take you out for lunch while I'm there. And maybe we can hit up target and see if there's anything you need."

"Luke…" Jess started the warning out of habit. This was familiar territory for them. Luke offering to buy stuff for him and him scolding Luke for treating him like a child. In this case, though, he really did need stuff.

"What? I want to get you a house warming present for your new place, and I don't know what you need, so I think it would make the most sense for us to go to target together and you can pick some stuff out and I'll buy it for you."

Jess sighed audibly.

"You must need something. Are you seriously telling me there's not one thing you can think of that you would like to have?"

Jess knew there was stuff he needed, and that Luke would wear him down eventually and he'd end up letting his uncle buy him a few things. But, he knew that Dean needed stuff more than he did. He knew he had to tell Luke about his situation and ask for his help. Not for the first time in relation to Luke, Jess thought about how this must be what it felt like to be the child of a loving and competent parent. One that he knew he could always count on for help, and who always prioritized his well being and wanted to make life easier for him whenever possible. Jess felt a swell of gratitude toward his uncle.

He answered truthfully. "Right now, Luke, I actually feel like I have everything I need."

"Oh, yeah?" Luke chuckled. "Lucky you."

"I am pretty lucky. But, I know someone who isn't. And he could use some stuff." Jess paused. "I need to tell you something, Luke."

"Ok, shoot." Luke didn't like the sound of this.

"You know how I told you that I ran into Dean?"

"Yeah. Did you see him again?"

"I did. But, uh, what I left out was that the first time I saw him, he was waiting in line at a homeless shelter near my apartment."

He could hear Luke processing from here. "What do you mean, Jess?"

"I mean, he's been living on the street."

"What? Why would he be living on the street?"

"I don't know."

"Did something happen to his aunt and uncle?"

"I don't know. I haven't asked how he ended up homeless. It felt like too much, since we aren't, or weren't, you know, really friends or anything."

"Jess. He can't be living on the streets homeless in this weather! He'll freeze to death! Where is he now? Ask him if he wants to come back to Stars Hollow. I can go pick him up and he could stay with me, or probably with Lorelai if he'd be more comfortable there, until he gets on his feet. I know she would want to help him, too. Wait, is his little sister on the street with him?"

"I don't know where his sister is, but right now Dean is at my apartment. I'm on my lunch break at work."

"He's at your apartment? Has he been staying with you?"

"He stayed the past three nights. I ran into him three days ago when he hadn't been able to get into the shelter for the night. He was sitting on some pieces of cardboard in an alley. I think he was planning to sleep there. I brought him home with me."

"Oh, Jess…" Luke felt relief that Dean wasn't out on the street, freezing and vulnerable. He also felt a swell of emotion at Jess' behavior. He needed a second to compose himself before he could speak without embarrassing himself.

"I told him he could stay for a while. Until he finds a place, I guess. So, he doesn't have to go back to the shelter."

"That's very nice of you, Jess." Jess could hear the warm smile in Luke's voice.

"I'll let him know he's welcome to stay with you, though, if he wants to go back to Stars Hollow. I'm guessing there's a reason why he's still here, but I don't know what it is. It seems like it would be much easier for him to be homeless in Stars Hollow, where he knows people who could help him." Jess reflected on how much improved Dean's life would be if he returned to Stars Hollow. He could stay with Luke, or Lorelai, or probably the families of some of his friends. Taylor would probably give him his old job back, or Luke would hire him on at the diner just to help him out. People would feed him and help him. He wouldn't be treated like an anonymous homeless person, who people avoided making eye contact with on the street. If Jess were homeless, he would prefer doing it in New York or any other anonymous city rather than in Stars Hollow, where he'd be the subject of town gossip and judging looks. But this was Dean. One of Stars Hollow's favorite sons. He would be welcomed back with open arms and offers of help in all forms. It hit Jess then, why Dean was still in New York. "I bet his sister is still here. I bet that's why he hasn't left the city."

"Oh, god!" Luke said. "What if something happened to his aunt and uncle, too? Maybe his sister got put in a foster home in New York and he wants to stay close to her."

"Could be. That would be crazy, though, if his parents died and then his aunt and uncle died so soon after. What are the odds of that?"

"Probably pretty slim, but I guess crazy things happen all the time."

They were both silent for a moment, reflecting on the unlimited possibilities of crazy things that happened.

Luke broke the silence. "So, Jess, you need some money? I know you've been barely getting by with your new rent and everything. And, now you'll be feeding Dean, too."

"Uh, yeah, I'm sorry to ask, but money would be great. Thanks, Luke."

"You didn't ask. I offered. And he must need stuff, too, right? I mean, does he have enough warm clothes and stuff?"

"I don't know. I mean, I doubt it. He's got this one backpack of stuff with him." Jess paused, remembering something from the previous morning. "He ripped a shirt yesterday trying to get it out of his bag. I think it got caught on the zipper of his jeans or something. He looked like he was ready to cry when he realized it was torn."

Luke felt a surge of sympathy for Dean. First losing his parents and now dealing with being homeless. No one deserved that. He needed to get money to Jess. He wanted to stock his nephew up on food, too. Get Dean some clothes. And toiletries. And whatever else he needed. He thought that kind of charity might be easier for Dean to take coming from him directly than from Jess.

"Jess, I think I should come out tomorrow instead of waiting for next Sunday. Is that ok? You have the day off, right?"

"Uh, yeah, I'm off. Tomorrow would be great."

"Ok, good. I want to get Dean some clothes and stuff, whatever he needs, and make sure you guys are all set with food and stuff. I don't want to wait a week. And I want to talk to Dean and make sure he knows he has options if he does want to come back to town."

Jess sighed with relief at the thought of Luke arriving tomorrow to help. He couldn't afford the food and other stuff that Dean would need on his own, but even more importantly, he wasn't sure how to talk to Dean about any of this. But, he knew Luke would be able to. He would use his parent voice and get Dean to open up about what was going on and be able to actually help him. Jess was proud that he had made the decision to take Dean in on his own, without Luke's counsel, but he felt a measure of relief that he wasn't in this alone anymore.

"All right. We have a lot to do tomorrow, Jess. So, I'm thinking I'll get on the road early, beat the traffic and aim to get to your place by nine, ok?"

Jess inwardly balked at the earliness of the time, but he knew Luke was right about them having a lot to do. And he wanted his uncle to have plenty of time to talk to Dean.

"Ok."

"And when I say nine, I mean I want you-"

"Up, washed and moussed and ready to go!" Jess finished for him with fake enthusiasm. "Yeah, I know the drill, Luke. I'll be ready."

Luke chuckled. "Sorry, nephew."

Jess smiled, knowing his uncle had nothing to be sorry for. "Thanks, Luke. I really appreciate this. I wasn't sure what to do. Or, if I could afford to feed both of us. Or, I don't know, how to actually help him…."

"I'm happy to help any way I can, Jess. Really. Your problems are my problems, kid. I mean that. And, Jess?"

"Yeah?"

"I'm really proud of you for helping Dean out like this."

Jess felt a small smile spread across his face. He felt better, more at peace with himself, than he had since the day he had first seen Dean in line at St. Sebastian's. "So, I'll see you tomorrow then."

"Looking forward to it, nephew."

Luke hung up the phone and yelled into the kitchen. "Hey Caesar! I'm going to take off for a while. I'll be back before the dinner rush. I've gotta go run some errands."


	4. Chapter 4 - Jess and Dean Talk

**Chapter 4 Notes:** More detailed notes are at the end of the chapter, because I didn't want to give away too much here, but I wanted to point out that some things in the Stars Hollow history of events have been tweaked. Thank you to everyone who took the time to leave me a review for the first three chapters. All reviews and feedback are welcome and much appreciated.

 **Disclaimer:** I own nothing except my own obsession with Gilmore Girls.

 **Trigger Warning:** Homelessness. Mentions of death and loss.

Jess folded down a corner to mark his page and closed the book he had been reading. He set it down next to his mattress and looked over to where Dean was lying on the floor reading Sports Illustrated. "Are you good if I turn off the light now?"

Dean looked up and nodded through a yawn. "Yeah, sure." He closed the magazine and put it aside, wiggling around until he got in a comfortable position to sleep.

Jess didn't know why he had put off telling Dean about Luke's visit all night. He knew he should give the guy some warning. As relieved as he was that Luke would be on his way to New York in a few hours, he was a little embarrassed to have his uncle rushing to his rescue. Luke had been out to see him twice since he had moved to New York and he had been back to Stars Hollow for a visit once as well, and it's not like Luke hadn't been planning to come out next week anyway, before anything had even come up about Dean. But, he couldn't help thinking that Luke showing up so soon after Dean got settled would look suspicious to Dean, as if Jess had called him for help. Which he had. But, still. Jess didn't want to look like a little kid who needed a grown-up to help him with his problems. He wanted to be the one helping Dean with his problem. He was also nervous about having violated Dean's privacy by telling Luke about his situation. He didn't expect Dean to be that upset. Dean seemed like the kind of kid who would have told his own parents things about his personal life and about his friends, especially if he had been helping a friend with a serious problem. And Luke was sort of like Jess' parent, so he was pretty sure Dean would understand why he had spoken to Luke. But, he still wished he had run it by Dean first, just in case.

Jess didn't get up right away to turn off the light switch. It felt too cowardly to have the conversation in the dark. "So, Luke is coming into the city for a visit tomorrow. I, uh, just found out today when I talked to him on my lunch break, and I just wanted to let you know…" Jess trailed off, feeling like an ass for springing this on Dean so last minute. "I should have mentioned it earlier, but I guess I forgot when I first got home." Jess immediately felt uncomfortable at the out and out lie.

"Oh…." Dean was surprised. "Ok. Um, what time is he getting here? I was planning to go fill out more job applications tomorrow anyway, so I can definitely make myself scarce while he's here and stay out of your way."

"Oh, no, you don't have to do that. That's not why I'm telling you he's coming." This conversation was already off to a bad start. "I mean, he knows that you're staying with me, and he wants to see you, too. He wants to take us out to lunch. Both of us. And…catch up with you, I guess." When Dean didn't respond, Jess filled the silence. "And, he mentioned something about Target, too. He usually tries to buy me a few things when he's here. I always tell him he doesn't need to, but he always ends up forcing stuff on me anyway. He's really good at wearing me down to the point where I can't handle hearing one more word being said about wool socks, or new underwear, or whatever else he's gotten in his head that I need, and I just give in to save my sanity. And, he'll probably want to put up shelves or fix something." Jess knew he was rambling now, and hiding his discomfort behind sarcasm, but he couldn't seem to reign it in. He felt like Luke when he was uncomfortable, trying to talk himself out of the awkwardness, but only making it worse. He couldn't understand why talking to Dean about anything important was always so nerve-wracking. "He did that when he came out to my last place. He seems to really like doing that kind of stuff, and I know he doesn't have anything all that exciting in his life now that I've left Stars Hollow, so hey, I figure if putting up a shelf or putting WD-40 on something squeaky makes the guy happy, who am I to deny him that? I mean there's little enough joy in the world as it is, right?"

Dean stared at Jess, wordlessly, clearly taken aback by the steady stream of nonsense coming out of Jess' mouth.

Jess took a breath, knowing he needed to cut to the chase. "So, uh, I told him about your situation. I really hope that's ok with you. I probably should have asked you first…." Jess tried to read Dean's reaction to determine if he was angry, but all Jess saw was a deer in the headlights. "Are you mad?"

"What?" Dean snapped out of his surprise. "No, I'm not mad. Sorry, I'm just a little caught off guard, I guess." Dean looked away from Jess for a moment. "You're the only person who knows about…my situation, and I'm just processing the fact that Luke knows now, too. But, no, I'm not mad." Dean smiled, but Jess could tell it was forced for his benefit. "It will be nice to see Luke. If you guys are really sure you don't mind me tagging along."

"We don't mind. I get the impression your presence is mandatory. I'm pretty sure I'd get an earful from Luke if you weren't around tomorrow. He was really worried about you when I told him what was going on. And, he asked me what you needed. Just to give you a heads up, he wants to buy you some stuff tomorrow, too, so you might want to start thinking about what you need."

Dean frowned. "That's really nice of him to offer, but I can't let him do that. It wouldn't be right. You're already doing so much for me by letting me stay here."

Jess laughed. "Yeah, I'm going to let you duke it out with him yourself on that one. Luke's a pretty chill guy for the most part, but he's not good at taking no for an answer if he thinks you need something. Trust me, he's going to buy you stuff. He was already asking me if you have enough warm clothes and everything."

Dean knew he would give in if Luke offered to buy him something. He would politely decline at first because his parents raised him with manners, but if Luke pushed, he realized with shame that he would let himself be persuaded, probably embarrassingly quickly. He would keep a list of what Luke spent and pay him back when he got a job, but he couldn't deny that he needed stuff now. Even just another shirt or two would be great. Or a couple pairs of socks or underwear. He had gone to the laundromat today so that he wouldn't smell funky when he had gone out to apply for jobs, but it would be nice to be able to have enough clothes to go more than a couple of days between loads, especially when he got a job and had to look presentable and clean every day. Laundry was a hassle and it was expensive. "It's really nice of him to be concerned about me. Do you think he's told anyone else in Stars Hollow?"

Jess thought about that. "I don't know. I mean, he doesn't talk to a lot of people or anything. He pretty much keeps to himself except for serving people in the diner. I could see him maybe telling Lorelai. He seems to tell her everything. But, that's probably it. I didn't tell him to keep it a secret or anything, though. Should I have?"

"No. No, that's fine. Yeah, you're right. I'm sure he's not spreading it around town or anything."

"I don't picture him running straight to Babette and Miss Patty with the news if that's what you're worried about."

Dean chuckled lightly. "Yeah, I'm sure you're right."

"He also wanted me to let you know that if you wanted to go back to Stars Hollow, he would take you back with him. He said you could stay with him until you got back on your feet."

Dean was lying on his side, head down, studying the pattern on the quilt he was laying on. "That's nice of him. Really nice. But, I can't do that."

Jess spoke carefully. "Things might be easier in Stars Hollow. You know people there. I bet Taylor would hire you back."

Dean nodded slowly. "Yeah, you're probably right."

"What about that girl?" Jess struggled to come up with her name.

Dean looked up. "What girl?"

"Tall. Blond. Pretty. The one you were dating after Rory?"

"Lindsay?" Dean frowned. "What about her?"

"Is she still in Stars Hollow? Are you guys still in touch? I bet she would want to help you out if she knew what was going on. From what I understand from Rory, you seem to be the kind of ridiculously considerate and ass-kissingly attentive boyfriend that a girl can look back on fondly even when she's no longer dating you."

Dean snorted. "Aww, Jess, I'm so flattered that you and Rory used to talk about me." Dean smiled at the scowl on Jess' face. "Lindsay probably would still help me if she knew what was happening with me. She's that kind of person. But she dumped my ass the day after the fight at Kyle's party."

"Oh, I didn't know that." Jess thought about Dean losing his girlfriend and parents all around the same time.

"Well, she had just seen me pick a fight with you over my ex-girlfriend. She was smart enough to know she deserved better than someone who was still hung up on his ex." Dean paused, thinking back on that time. "Her whole family still came to my parents' funeral, though, a couple weeks later. Her mom sent over so much food. And Lindsay came by the house the day…when it happened…before my aunt and uncle had even come in from New York. She brought dinner and wanted to make sure we were ok. She ended up crying as much as we did. She hung out with me and Clara all night and all three of us slept in Clara's room that night. Clara really liked Lindsay."

Jess saw an opening for a question, and hoped he wasn't being too invasive. "Where is Clara living now?" As soon as he got the question out, he cringed at his wording as the idea hit him that Clara might not be living anywhere. Maybe she had been in an accident with her aunt and uncle and Dean had lost all of them at once. He rushed to backtrack. "I'm sorry. You don't have to tell me anything. It's none of my business, really."

Dean was lying on his back, hands clasped behind his head, gaze fixed on the ceiling. When he was sure he wasn't going to cry, he turned his head toward Jess. "It's ok. Clara is living with my aunt and uncle just outside the city. That's why I can't go back to Stars Hollow. I want to be near Clara and be able to see her."

Jess knew he was prying now, but he really wanted answers. And this was the most open Dean had been about his recent past since he and Jess had reconnected. "So, uh, why aren't you staying with them, too?"

Dean looked back toward the ceiling and took a breath. "I was at first, but I had to leave. I did something really stupid and they didn't want me to stay there anymore."

Jess was intrigued. He couldn't reconcile his mental image of perfect little brown-nosing Dean with a guy who did something bad enough to get himself kicked out of someone's house. He had never met an adult, including his own uncle, who wasn't a member of Dean's fan club. He sensed it was better to not press for details and just let Dean talk.

"I, um, this is really embarrassing. It's easily the worst thing I've ever done."

Jess was afraid to move, or even breathe, not wanting to jar Dean out of his train of thought when he was so close to getting answers.

"I kind of slept with my cousin's fiancé."

"Oh, shit." Jess didn't know what to say. He knew he had to be replicating the deer in the headlights look he had seen on Dean earlier, but he couldn't help it.

"He had brought her home from law school with him for Thanksgiving weekend. We thought everyone else was asleep, but my cousin walked in on us. He lost it. Pulled me away from her and beat the shit out of me. Woke up everyone else. By the time my uncle got him off me, I was a mess. I was on the floor with a bloody nose and my sweatpants down around my knees. It was so humiliating. Millicent was next to the bed putting her clothes back on. I remember Kevin calling her a cheating whore before he stormed out. I was pulling my pants back up and my uncle was screaming at me about what a disgrace I was. That I was just like my father, weak and selfish with no respect for other people. He said he was glad his sister wasn't alive to see that I'd turned out just like my father because it would have broken her heart. I remember Clara standing there watching. My aunt was hugging her and trying to pull her out of the room and Clara was just standing there crying her eyes out. My uncle told me to pack my shit and get out. So, I did. I grabbed my jacket and shoved anything I could grab into my backpack. I stopped to hug Clara and tell her I love her and that everything was going to be ok, and I remember my uncle shoving me toward the door, away from her. And Clara…" Dean's voice took on a choked-up quality. "Clara was crying and screaming for me to wait. My aunt was holding her back. Clara was yelling that she wanted to come with me. But, she couldn't. I mean, I didn't even have anywhere to go."

"Oh, shit." Jess repeated, unable to think of anything else to say. He hoped he didn't look as shocked as he felt. He tried to school his features into a neutral and non-judgmental expression in case Dean looked his way. But, holy shit! "Wait, why did your uncle compare you to your father?"

Dean sighed. "My dad, he uh, cheated on my mom in Chicago. He had an affair with this woman. She was married, too. Her daughter was friends with Clara. I guess it had gone on for a few months. My parents almost got divorced when my mom found out. My uncle is a lawyer, so my mom told him what happened and asked for legal advice about divorce. That's why we moved to Stars Hollow. So that we could all get a fresh start away from the woman my dad was seeing. Things were good in Stars Hollow. My parents seemed like they were doing better. My dad was more involved in family stuff again. He seemed less distant, and just less depressed, in general. We built that car together. Everything seemed like it got back to how it used to be, before the affair. It was good. My uncle never got over my dad cheating on his sister, though, and pretty much refused to be around him after that. But, that wasn't any great loss, cause my uncle's always been kind of a dick."

"I remember hearing my parents fighting one night when we were still in Chicago. They thought I was asleep. I remember my dad telling my mom that he never loved Susan. That was her name, the woman he was seeing. That she had just made him feel good about himself at a time when he had felt bad about pretty much everything. Like, he had just lost his job with a company he had been with for pretty much my whole life, where he made good money. He hadn't done anything wrong. He didn't get fired or anything, but his company had downsized and let him go. And he wasn't taking it well. He was really depressed. My mom worked, too, but she still did most of the stuff at home for me and Clara because we were all used to my dad working longer hours, so we didn't really need him for stuff, you know. Looking back, I think he must have felt really useless then. And I guess Susan made him feel better. At the time, I remember being so pissed! Like, what the fuck kind of explanation was that for hurting my mom, and my whole family, the way he did. It was so selfish and gross. I spent a long time hating him after that. For cheating on my mom to begin with and then for having such a pathetic and shitty excuse."

Dean sighed. "But, now it freaks me out that I can understand it better. Me and Millicent. It wasn't about love, or even sex. My uncle is kind of a jerk. My aunt is a nice person, but just really quiet and reserved. I didn't feel like I had anyone to really talk to about how I was feeling. And Kevin brought Millicent home and she was just really nice to me at a time when I just felt so shitty and lonely and so scared about everything. She asked about my parents and how I was feeling and really listened to me without giving me some 'it'll all be ok' bullshit, which seemed to be all I got from my aunt and uncle. She seemed to really care, about some eighteen-year old kid she'd just met. I was trying to be there for Clara, but I felt like I didn't have anyone there for me. Millicent made me feel heard, I guess, and just…less alone. And one night, she got up to get a glass of water and heard me crying in my room and came in. I was having a really bad night. I couldn't sleep. I couldn't think of anything but my parents, and how they must have felt, how scared they must have been, when it happened. At first, she just held me while I cried, and listened while I talked about my parents. I remember her rubbing my back and pushing my hair off my face. At first, she could have been anyone, you know, even my mom. I mean, she was pretty, but I honestly hadn't thought about being into her before that. Then, I don't know. I'm not positive who even started it, but we were kissing, and then, I don't know, other stuff happened. And then Kevin came in…And, well, now I'm sleeping on your floor." Dean sighed. "I guess that brings you up to speed on my life…...I'm sorry if that was more than you wanted to know. I didn't mean to dump all that on you, Jess. I think I just really needed to tell someone."

"Hey, it's ok. You didn't dump on me. I told you that you could talk to me, didn't I?"

Dean nodded. "You did, yeah, but sometimes people just say stuff like that. Doesn't always mean they want to deal with your shit or anything…Thanks for really listening to me, though. And I know it makes you uncomfortable when I thank you, but really, Jess, thanks for letting me stay here and not turning your back on me in the alley that night. I would have deserved it. I was terrible to you in high school. I really appreciate how great you've been to me. Really. Thank you." Dean's voice started to choke up again and he felt dangerously close to crying.

Jess' instinct was to blow off Dean's words with some kind of sarcastic comeback, but he realized that would be shitty in light of everything Dean had just shared with him. He would be saving himself from discomfort, but at Dean's expense. He also had questions. Had Dean spoken to his aunt and uncle since Thanksgiving? Or his cousin? Where had he gone the night he left their house? Was he still in touch with his sister? How long had it taken him to run out of money? How long had he been sleeping in shelters? But, he decided bombarding Dean with questions when he was vulnerable wasn't the right way to go. Now wasn't the time to satisfy his own curiosity. He knew he wouldn't want to be pushed, if he were in Dean's shoes. He would be patient and let Dean tell him things when he chose to. Jess opted for the simplest response. "Your welcome."

Dean turned his head away from Jess and lay down on his pillow, thinking about everything he had just shared with Jess. "What time did you say Luke's getting here tomorrow?"

"Oh, uh, nine o'clock." Jess took the cue that they were done with the serious conversation portion of the evening and responded accordingly. "I know it's ridiculously early for a Sunday, but Luke is pretty much morally opposed to anyone sleeping in, ever. I'm thinking he needs to take us out for breakfast to make up for getting us up so early. I could really go for some bacon and sausage, and hash-browns." Jess gets up and flips the switch to turn off the overhead light and gets back into bed in the dark. "I don't think I've had a real breakfast since the last time I was back in Stars Hollow at the diner."

"Breakfast does sound really good." Dean shut his eyes, feeling a little lighter at having finally shared his story with someone. Everything seemed a little less hopeless now that he had told Jess. He thought back to Jess' shocked reaction to his story. He was surprised to realize that he trusted Jess now. A year ago, he never would have thought that would be possible.

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The next morning found Luke in his truck heading to New York, looking forward to seeing Jess and worrying about Dean. When he had left Stars Hollow almost two hours ago, he had had the road pretty much to himself, but more and more cars were joining him the closer he got to the city. Luke usually made it a point to avoid New York altogether and only venture into Hartford when absolutely necessary. It was a testament to how much he loved his nephew that he was making his third trip to New York in the past six months. He could deal with being out of his comfort zone for a day to make sure Jess was ok and had everything he needed. And now, Dean. Luke sighed. The idea of Dean living on the street, cold and alone, so soon after losing his parents made something in Luke's chest ache. He could remember how hard it had been when his own father died when he was nineteen. He had at least been left with a business to run and a place to live in the town he had grown up in. He couldn't imagine having to go through that loss by himself, homeless and scared, in a city like New York. He was very glad that Jess had run into Dean when he had, and he was so proud of his nephew for helping Dean out like this, especially considering their less than amicable history together. Luke reflected on his own history with Dean. For the most part, he knew Dean was a good kid, but Luke also knew that he hadn't always been that nice to him when the boy had been dating Rory. He thought in particular about the time he had physically tried to block Dean from entering the diner after he had broken up with Rory the first time and wondered if he should try to apologize to Dean about that. He decided he'd see how the day went. It might be awkward enough without bringing up past issues.

When Luke had learned about Dean's situation from Jess yesterday, he had immediately wanted to help. He had driven to the large grocery store on the other side of town and picked up some groceries that would survive the trip to New York, cans of soup, chili and tuna, power bars, beef jerky, a loaf of whole grain bread, bags of apples and oranges, peanut butter, fruit preserves, rice, pasta, dried fruits, and nuts. He had three full shopping bags of stuff. He had run into Lorelai in front of the diner as he was coming back from the hardware store in town. He had gone in to purchase a plug-in smoke and carbon monoxide detector, along with back-up batteries. Not for one second did he trust a landlord who wasn't smart enough to properly renovate a rental unit with his nephew's safety. He had also picked up a first aid kit, emergency flashlights, a fire extinguisher, and a solar powered emergency cell phone charger while he was at it. The diner had been starting to fill up for dinner and Luke hadn't wanted anyone to overhear their conversation, so he had ushered Lorelai upstairs, where he filled her in on what was going on with Dean. He wasn't sure Dean wanted anyone to know, so he had asked Lorelai to please not mention anything to Rory until he got a chance to talk to Dean. Lorelai had been heart-broken at hearing what Dean was going through. Luke knew she had a soft spot for him from his time with Rory, something she had never developed for Jess. She had asked to tag alone, but Luke had told her that he didn't think it was a good idea this time. He had explained that he didn't want to just show up at Jess' place with Lorelai without asking Jess if it was ok first. Plus, he still hadn't told Jess that he and Lorelai had started seeing each other. He explained that he wanted to tell Jess about them on his own and then maybe Lorelai could come the next time he went to the city. He hoped he hadn't said the wrong thing. Lorelai had said she understood his reasoning for not wanting her to join him, and that she was ok, but Luke had learned early in their relationship that that didn't always mean that she was. He honestly didn't know how Jess would feel about Lorelai tagging along even if he had asked in advance, but he knew that Dean was the draw for Lorelai, not Jess, so the issue may never come up again once Dean was no longer staying with Jess. Plus, he normally liked his one on one time with his nephew during these visits. He knew there would be tension if Lorelai was there, too. He worried that he was doing exactly what Nicole, and Rachel before her, used to accuse him of, and not letting Lorelai fully into his life. Keeping her at a safe, non-threatening emotional distance was how Nicole had put it. He wished Lorelai and Jess got along better. The balance was difficult for him. He wanted Jess to appreciate the same things he did about Lorelai and enjoy her company, and if things got serious between them, he wanted Lorelai to care for Jess and have the same parental feelings toward him that Luke had for Rory. But, he couldn't see that happening. Lorelai had left the diner without eating the burger she had come for and that had worried Luke. But, she had returned twenty minutes later with a big smile and a Doose's Market bag full of what she proclaimed to be Dean's favorite movie night snacks. Luke had poked through the bag while Lorelai ate a burger and fries at the counter. Oreos, Mallomars, four kinds of Pop-Tarts, salt and vinegar potato chips, chocolate covered pretzels, the makings for s'mores, and gummy bears, not worms, because apparently Dean did not appreciate his gummy candy in worm form. Luke had been appalled at the contents of the bag but had promised to deliver them to Dean anyway. He figured Dean's diet probably hadn't been very healthy when he had been homeless and the last thing the kid would need was a bag full of sugar, but he also realized that right now, Dean might be grateful for any kind of care package that showed that someone, well, cared. He had kissed Lorelai and told her how thoughtful she was while he had made a mental note to run over to Doose's once Lorelai left and pick up some multi-vitamins to help counter-balance the effect of her purchases.

As Luke neared the address Jess had given him, he started to get nervous wondering how the day would go. He had come up with so many things he wanted to buy for Dean the night before that he had sat down and made a list. He reminded himself again now that Dean wasn't his and he couldn't force things on him for his own good the way he did with Jess. He really hoped that Dean would let him help him and that he didn't have the same stubborn attitude as Jess. Luke reflected on how crazy things had worked out, and how it would have made more sense for Jess to be the one to end up in this situation instead of Dean. Dean had been a well-liked and well-adjusted kid with a happy and stable family life, while Jess had received very little in the way of security and support from his parents, with a father who had abandoned him when he was just a baby and a mother who had been so tired of dealing with him that she had wanted him out of her home by the time he was seventeen. Luke couldn't help but think about how easily Jess could have ended up in Dean's shoes if his life had gone even slightly differently than it had. If he had just taken off on his own instead of allowing himself to be sent to live with an uncle he barely knew in Stars Hollow. If he hadn't had an uncle to get sent off to. If he and Jess hadn't gotten along and Jess hadn't stayed. Luke was grateful that Jess was doing ok and that they had gotten to the point where Jess was willing to accept help from him. But, if he hadn't. If Jess had been the one to end up homeless and hungry, Luke would want someone to help him, the way he planned on helping Dean. Luke sighed and started looking for a parking spot. He really hated the city.

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 **Notes:** Even though it was a brief mention, I really wanted to make Lindsay normal and reasonable in this story. One thing that always bugged me about the show was the stable of disposable female characters that male characters just seemed to bide their time with while waiting for a Gilmore Girl to free up and date them. Lindsay, Shane, Nicole, Sherri. They were never well developed to begin with and always seemed to lack understandable motivation for the decisions they made, like Lindsay agreeing to marry Dean so soon after he got in a fight over an ex. Nothing about that ever made sense to me.

As for Dean, I don't dislike his character as much as many fans of the show do, but I always saw his weakness as being, well weakness, and clinging onto women in a very unhealthy way, first Rory, and then Lindsay when Rory hurt him, and then Rory again even while he was married to Lindsay. I feel like having him sleep with a woman because he himself was hurting, without thinking about the fallout for his family or for her, seemed like something he would do.

Any and all feedback is appreciated. Thanks for reading!


	5. Chapter 5 - Luke's Visit - Part I

**Chapter 5 Notes:** I want to clarify the timeline in response to a question from a reader after the last chapter. This story is set prior to Jess' publishing house days in Philadelphia. In the alternate universe of this story, Jess still runs off to California to see Jimmy, but things diverge from cannon when he returns to Stars Hollow after a short time in California and reconnects with Luke prior to moving to New York. Jess and Dean are nineteen here and it is their first winter following high school. Also per a reader comment that the length of my paragraphs in the last chapter made them difficult to read on a mobile device, I tried to keep them shorter and more manageable in this chapter. Thank you to everyone who is reading this story and especially to those who have taken the time to leave me reviews. As always, you are greatly appreciated.

 **Disclaimer:** I own nothing except my own obsession with Gilmore Girls.

 **Trigger Warning:** Homelessness. Mentions of death and loss.

Luke pushed the doorbell to Jess' apartment and heard the responding buzzing noise that signaled Jess had remotely unlocked the door. Luke quickly let himself in, juggling two full shopping bags in each hand, cradling a fifth bag in one arm, and his camping bedroll in the other. He had had to park a block and a half away, and even though he wore thick gloves, his fingers were already tingling from the cold. It felt even colder here than it had when he had left Stars Hollow a couple of hours earlier. He climbed the flight of stairs to Jess' apartment, hitting the landing just as Jess pulled open the door to his apartment. The kid looked barely awake, and was dressed in pajama pants and a sweatshirt, his hair a disheveled mess. Luke felt a warmth spreading in his chest and grinned at the sight of his nephew looking like a sleepy little kid.

"Hey, Jess." Luke put his load down just inside Jess' apartment and reached out an arm to pull his nephew into a hug.

"Cold!" Jess squawked, jumping a step back from Luke's touch. "You're freezing! Jeez, Luke, take off your coat and gloves first before you get anywhere near me!"

Luke laughed. "Sorry, kid. It's good to see you."

"You, too. Thanks for coming."

Luke pulled off his outerwear and looked around the apartment for a place to hang his jacket, taking in the mattress, the pile of quilts on the floor that he assumed was Dean's bed, the lack of a table or chairs and the tiny kitchen area that looked like it would be more at home in a small camper than an apartment. "Am I supposed to just add my stuff to the pile here?" He tilted his head to indicate the pile of coats, gloves and hats on the floor by the door.

Jess smirked. "Hey, you catch on fast."

"No closet, or coat rack or anything, huh?" Luke asked as he laid his jacket down on top of the pile.

"I'm all about minimalism these days, Luke. Less is more, and all that. Or at least I was until you showed up with everything you got there." Jess nodded toward the shopping bags Luke had brought in. "And instantly doubled the amount of shit in this apartment."

Luke chuckled and took a step toward Jess. "Can I hug you now, smart guy?"

Jess shrugged. "If you must." He could still feel a chill emanating off Luke from his time outside, but this time he didn't protest, and let himself be pulled into a hug.

Luke held Jess knowing that this brief moment was the only upside to having his nephew live so far away from him. Now that they saw each other less frequently, Jess tolerated being hugged at the beginning and end of their visits. It didn't make up for not having Jess in his daily life anymore, but it was something. He had never been brave enough to try hugging the boy during the entire two years he had lived with him. He had done it for the first time when Jess had turned back up at his door late one night after his failed experiment with Jimmy in California. Something about Jess seeing Luke's apartment as his home, where he could recover from his trip and get his bearings before moving to New York, had given Luke the confidence.

Jess pulled back first. "You find the place ok?"

"I did. Your directions were very clear. Thank you."

"So, what is all that stuff anyway?" Jess yawned, angling his head toward the shopping bags. He would normally make a fuss about Luke spending so much money on him, but this time, he just felt grateful that Luke had likely stocked them up on food for a few weeks by the look of the bags.

The bathroom door opened and Dean stepped into the room, dressed in jeans and a sweater, an unsure expression on his face. "Hey Dean!" Luke took a couple of steps past his nephew and extended a hand to Dean as he clapped him on the shoulder with the other. "It's really good to see you."

"You, too, Luke." Dean smiled as he shook Luke's hand.

"I was just about to show Jess what I brought you guys. I've got some stuff for you, too."

"Holy shit, Luke!" Jess called from where he was crouched down, already poking through one of the bags. "Did you have a lobotomy since I last saw you?"

"What are you talking about, Jess?" Luke turned toward his nephew.

Jess held up a box of Pop-tarts and a package of Oreos. "You never let me have stuff like this when I lived with you. You once lectured me on the food pyramid for twenty minutes for looking at a package of Oreos at Doose's. Just for looking at them. With my eyes. What the hell happened to you since then?"

"Oh, that? That bag is from Lorelai. She asked me to bring it." Luke turned back to Dean. "I want to go on record that I don't approve of anything in that bag, but she swore it was all your favorite stuff."

Jess was pulling out the graham crackers, marshmallows and chocolate bars. "S'mores, seriously? In the mood to relive your boy scout days, Dean?"

Dean laughed. "Wow, that was really nice of Lorelai."

"She swears you loved this crap."

"Yeah, I did. My mom hardly ever bought us junk food, so yeah, I pretty much went nuts when I'd go over to the Gilmore's for movie nights. Lorelai bought all the best crap. Thanks, Luke. And please tell Lorelai I said thank you, too."

"I will. She says to tell you that she's thinking about you and that you should call her if you need anything. She wanted to come out here today, too, but I didn't think it was a good idea…...what with everything with her and Jess. But, if you guys come back to visit sometime, she'd love to see you."

"What do you mean, everything with Lorelai and Jess?" Dean looked puzzled. "Jess, do you not get along with Lorelai?"

Jess looked up from where he was now pawing through a second bag, a small fire extinguisher in his hand. "Not so much."

Dean laughed. "Are you kidding? Everyone likes Lorelai. She's so much fun. She barely even acts like a mom. Not liking Lorelai is like not liking, I don't know, the circus or something."

Jess refocused on the contents of the bag in front of him. "I hate the circus. But, huh, I can appreciate the parallel you're making between Lorelai and a circus clown. Both obnoxiously loud, in sound and wardrobe."

"Jess…..." Luke scolded playfully.

"Both think they're much funnier and more whimsical than they really are."

"C'mon, Jess, cut it out." Luke warned.

"Both constantly crave the spotlight, and like all attention-whores, they-"

"Jess!" Luke cut in sharply, voice raised. "Watch it!"

Jess looked up curiously at his uncle's reaction. "Um, ok, sorry, I guess." He placed the flashlight he was holding on the floor and got to his feet. "Thanks for all this stuff, Luke. We really needed it."

Luke had calmed down and was feeling like he may have over-reacted. "You're welcome, Jess. And, I'm sorry for snapping at you."

Jess nodded. "It's ok." He had learned early on with Luke that even though his uncle sometimes raised his voice, he never actually believed that yelling at Jess was the right thing to do, and he always felt guilty afterward. He had also learned that Luke usually revisited the topic of the behavior that had caused him to raise his voice with a strongly worded lecture, later on, when he felt composed enough to speak to Jess more constructively about it. Jess wondered if he still had the reprimand coming, or if Luke deemed him too old for that now. "So, I should probably go shower so we can head out. You're taking us out for breakfast, right, Luke?" Jess smiled and clapped Luke on the arm as he walked by. "It's the least you can do for dragging us out of bed at the crack of dawn on a Sunday."

Luke returned the smile. "Sure, I can do that. I thought you were going to be ready by nine, nephew. Do you remember that plan at all?"

"Huh. That does sound familiar. I guess we overslept. Then I selflessly offered my guest the shower first, so that I would be the only one who got bitched at for running late when you got here."

"Well, hurry it up, Jess. We have things to do." Luke picked up two of the bags of food and brought them closer to the kitchen area of the apartment. "I'm going to start putting this stuff away while you're in there."

Jess frowned as he pulled clothes out of one of his plastic storage containers. "But, you don't know where anything goes. You'll mess up the grand order of things in the kitchen."

"Jess, your 'kitchen', and I use the term loosely, is the size of a postage stamp. I think I can figure it out. Go shower."

Jess grunted and disappeared into the bathroom.

Dean picked up the other two bags of food and set them down closer to Luke. "So, um, I'm sorry for baiting Jess about Lorelai. I didn't realize you were serious about them not getting along. I didn't mean to start anything."

"Oh, that? Don't worry about it, Dean. It's not your fault. Jess has issues about Lorelai, but she's important to me, so…I just wish Jess would start acting like an adult about it. He doesn't need to be friends with her, but at this point, I'd like to see him be mature enough to not make fun of her just to piss me off, you know."

Dean nodded, not sure what to say. "Do you want any help? I can put that stuff away if you want, Luke."

"It's ok, Dean. I've got it." Luke smiled. "Plus, it gives me a chance to check out what you guys have been eating." Luke opened the cabinet above the counter, frowning at the meager contents, a lonely can of chicken soup and half a package of crackers. "Which is apparently not much." Luke started placing cans of food into the cabinet. "So, how are you doing? Jess told me what was going on with you. I was really sorry to hear that you were in such a tough spot."

Dean picked up Luke's use of the past tense, that he 'was' in a tough spot, and it sparked a warm feeling of gratitude for how much his situation had improved during the last week since he had run into Jess. "Thanks, Luke. I appreciate that. It's been really hard." Dean averted his eyes for a moment, forcing himself not to get emotional and embarrass himself. "I'm really grateful for everything Jess has done for me, though. He's been so great. Taking me in like this. Feeding me. Just having someone to talk to again has been amazing."

Luke smiled. "Yeah, he's a pretty good kid. I'm really glad you two ran into each other. I hate thinking about you out there in the cold all by yourself. Hell, I hate thinking about Jess out here in the city all by himself."

"I want you to know, Luke, that I'm looking for a job and as soon as I get one, I'm going to start paying Jess rent to stay here, and I'm going to pay him back for everything he's done, and spent, on me. I swear. It's important to me that you know that. I appreciate everything he's done for me and I don't want you to think that I'm taking advantage of him."

"Dean, I'm not looking at this as you taking advantage of Jess. Ok? Please don't worry about that. Everyone needs help at one time or another. You're a good kid, Dean. And a hard worker. You'll get back on your feet. I know you will. In the meantime, it's ok to let people help you. Jess wants to help you. So, do I." Luke folded an empty paper bag and moved on to unpacking the next one. "I really want to help you with anything you need today, Dean. Like clothes, toiletries, whatever you need."

Dean declined on reflex. "Oh, no, you don't have to do that, Luke. I'm ok." Dean cringed in embarrassment, knowing he didn't sound convincing even to his own ears.

"I know I don't have to, but I want to. You're already dealing with a lot, Dean. I don't want you worrying about how to afford toothpaste and socks on top of everything else." Dean felt tears welling up at Luke's open generosity and didn't trust himself to respond. Luke mistook Dean's silence for resistance. He stopped stocking the cabinet and made eye contact with the boy. "Look at it this way, Dean. If the situation were different. If I were gone and Jess was in your shoes, I would want someone to help him. And I didn't know your parents very well, but I know they were good people, the kind of people who would have helped Jess, or any kid they knew, who was going through what you are now. I know they were like that just from the kind of person you are. And I think they would want to know that someone was helping you, too. Don't you think?"

Dean nodded, with damp eyes. Luke put a hand on his shoulder and squeezed. "I'm sorry. I didn't mean to upset you. My dad died when I was around your age. And my mom had already been gone a few years by then. I know what it feels like, and I just want to be here for you and help you out any way I can. You're not alone. OK, Dean? I want you to know that."

Dean nodded again, eyes trained on the floor at his feet. "Uh…" Dean didn't trust himself to speak without losing control of his emotions.

"It's ok, Dean." Luke patted the boy on the shoulder and pulled his hand back. He felt guilty for bringing up Dean's parents so soon and wanted to change the subject. "Oh, hey, I brought you my camping bedroll. It's over by the door if you want to check it out. It's pretty comfortable. It'll be a lot better on your back than sleeping on the floor. Plus, you can roll it up and stick it in a corner or something during the day so it's not in your way." Luke watched Dean obediently go over to look at the rolled-up mattress. "I think you'll like it."

Dean sniffed. "Thanks, Luke. Really."

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When Jess was finally ready, the three went out for a late breakfast at a restaurant near Jess' apartment. After they ordered, Luke took out his list of things to get done that day, much to Jess' amusement.

"What, did you seriously write down things like, 'Buy Dean Underwear'?"

Luke took the pen out of his pocket and started making revisions, now that he had seen the state of Jess' apartment. "Underwear did make the list, my friend. What's wrong with that? If we don't write stuff down and go about things in an organized manner we could miss something. And I want to make sure you guys are all set before I leave today."

"Jeez, Luke. What else is on there? And what are you adding to it now?"

Luke looked up from his notepad. "I'm adding things that I think you need after seeing your apartment. Like wall hooks for coats. Something for Dean to store his clothes in. Stuff like that. And if you don't mind, I'd like to get it all written down before I forget something. Then we can all go over it together." Luke returned to scribbling in his note pad.

Jess looked at Dean, who was sitting quietly, looking slightly embarrassed. "Sorry about him." Jess angled his head toward Luke. "He's kind of a control freak. I should have warned you about that."

"Hey." Luke interrupted without looking up. "Just because I'm not looking at you doesn't mean I can't hear you, nephew."

Dean chuckled, feeling a little uncomfortable. "I really don't need that much, Luke. I mean even if we just picked up a couple of things, I'd be really grateful. And, thanks for letting me borrow your camping mattress. I mean, that's already going to help so much. Seriously."

Luke put the finishing touches on his list and looked up, with a small smile. "It's no problem, Dean. It will make me feel a lot better knowing you're not sleeping on the floor. That can't feel good on your back night after night." Luke stared at Dean, taking in his long shaggy hair protruding from under his knit hat. Dean had borrowed Jess' razor yesterday to shave before going out job hunting, but he hadn't been able to do anything about his hair. "You want a haircut today, Dean? I think you could use one."

Jess snorted out a laugh. "Jeez, Luke! Take it easy on the guy! What's next? You going to give him fashion advice? Hook him up with a wardrobe of flannel shirts and a baseball cap?"

Luke shot his nephew an admonishing look. "I'm just thinking, if he's out looking for a job, he wants to look as put together as he can. That's all I'm saying."

"I would love a haircut." Luke and Jess turned their attention to Dean. "Luke's right, Jess. I was embarrassed about my hair yesterday when I was out filling out applications. I look like a mess. I think a haircut would help me look more presentable when I'm applying for jobs. Thanks, Luke. And, I'll pay you back for everything today. I promise."

Luke dismissed Dean's offer with a wave of his hand. "Please don't worry about that, Dean." Then turned to his nephew. "See, Jess? Sometimes I know stuff?"

Dean laughed, starting to feel a little better about everything. He knew it was a ridiculous thought, since he was technically no longer a child, but he still felt relieved that a real grown up was taking over and managing his life, even if only for a day.

"Nephew, your first job is to find us a barbershop."

Jess watched Dean fidget uncomfortably next to him, and smirked. "Um, actually." Dean started. "I usually go to a salon, not a barbershop."

"A salon?" Luke pronounced it slowly as though repeating a word in a foreign language. "Men go to those places?"

"Yeah, lots of them do. So that they can see stylists instead of barbers. I go to a salon because my hair is longer." Dean pulled off his hat and ran a hand through a chunk of his hair, pulling it away from his head to illustrate the length. "And stylists are better with long hair. They're better at well, styling it I guess, so that it falls well and looks more flattering."

"So, it falls well?" Luke repeated. Jess was trying not to laugh at his uncle's earnest expression.

"Yeah, barbers are more into using clippers on short hair instead of creating styles for long hair."

Luke nodded seriously. "Huh. Well, you learn something new every day."

Jess smirked. "And, now a break from this episode of Queer Eye for the Straight Guy for a message from our sponsors."

Dean and Luke laughed, and Luke smiled warmly at his nephew, before looking toward the waitress to thank her for the drinks she was setting down on their table.

"What else have you got on your list, Luke? I bet Dean would like to know what else you've got in store for him today. Perhaps a mani-pedi following his hair cut?"

"All right, smart guy." Luke picked up his notepad. "Here's what I'm thinking. Let me know if there's anything on here you already have, or if I don't mention something that you need. Ok, Dean?"

Dean nodded. "OK."

Luke started reading items off his list, sometimes pausing to explain why he thought something was needed, or to gently shoot down one of Dean's protests that he deemed unreasonable. Jess interjected only once, when they got to thermal long underwear, to let Luke know that he could also use some to layer under his clothes for his commute to work. He started tuning his uncle out as the man rattled off a list of toiletries. He sat sipping his tea and watching Luke's face, as his uncle warmly encouraged and cajoled Dean into letting him keep certain things on the shopping list. It had always been weird to Jess that Luke seemed at his happiest when he was helping someone else, but he had come to know it was true. In Jess' mind it had always seemed like a personality glitch in his uncle, almost a flaw, to put someone else's needs before your own, but one that he was constantly grateful for nonetheless. And maybe one that he was starting to understand a little better.

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They hit Target first and had to make a pit stop back at the apartment to drop off their bags before moving on to a grocery store for perishable items like vegetables, eggs, cheese, and sliced turkey, followed by another stop at the apartment to put the food in the fridge, then a hardware store, a hair salon, and an REI because Luke hadn't been satisfied with the quality of the thermal layers at Target. They ended their day of shopping at Ikea and took a cab home with their purchases since Jess had convinced Luke that taking the subway would be significantly less of a hassle than driving his truck all over the city.

Back at Jess' apartment, Luke was installing a collapsible table into the wall. The table top would lay flat against the wall to save space when not in use but could be swung up and supported on two pullout legs when they wanted to use it. Luke had had to convince Jess to let him buy the table and the two matching folding chairs. Jess had been worried about the dining set taking up too much space, but Luke had pushed for it, alleging that it wasn't good for digestion to eat all their meals standing at the counter or hunched over their food on the floor like animals. Luke had asked for an opinion from Dean, who had been trying to stay out of the argument because it wasn't his apartment or his money, but since he was too respectful to ignore a direct question, he had admitted that it might be nice, and feel normal, to eat at a table. Jess had given in then. Luke had smiled. He had packed his toolset in the cab of his truck this morning just in case.

Jess and Dean had put up the hooks and hung up the coats that had previously lived on the floor. Dean had gone through the clothes Luke had bought him, carefully removing the tags and neatly folding each article before placing it in his new small plastic chest of drawers that matched Jess' and could be stacked to save floor space. Jess had carved out some space in the bathroom cabinet and organized Dean's new toiletries. Having finished their tasks and Luke having declined their help with the table, both boys were now lying around, Jess reading on his mattress and Dean lying on his new bedding playing with a ball, relaxing after a long day of shopping while Luke finished up with the table.

Luke glanced out of the corner of his eye at the boys while he worked at tightening the last bolt. He felt like the day had gone even better than he had expected. Dean had been a mostly willing participant on the shopping trip, obediently picking out things as Luke instructed. Only a few times did Luke have to send him back to replace something cheap and flimsy with something more substantial, like when he had selected a two-dollar bag of disposable razors, and Luke had encouraged him to replace it with a real razor and refill cartridges, claiming that no one preferred the disposable kind. Luke watched now as Dean repeatedly threw a baseball-sized rubber ball in the air over his head and caught it. The kid had picked up the ball early into their time at Target and had kept fidgeting with it, tossing it back and forth between his hands as they shopped. As they were loading their purchases on the conveyor belt at checkout, Luke had asked if Dean wanted to take the ball, too. With an embarrassed look on his face, Dean had said no and set the ball down on the magazine rack next to the register. Luke had picked it up and put it with the other things to be rung up, saying they would take it in case Dean changed his mind. He figured Dean wasn't too old to deserve a toy for good behavior at the end of a shopping trip, and he had chuckled when Jess had made a comment teasing Dean about the same thing.

Luke put down his wrench and, still kneeling by the table, turned to face Jess and Dean, surveying the apartment. He felt much better about everything than he had a day ago. He liked knowing that he'd be leaving them with a well-stocked kitchen, and a better organized and more comfortable home. At Luke's urging, Jess had picked out a couple of warm things, and Dean now had enough warm clothes, socks and underwear to go a few days without doing laundry, as well as an interview outfit, complete with pants that weren't jeans, a nice shirt, and shoes that weren't sneakers. Luke felt proud of what they had accomplished, and he hoped the kids had enjoyed the day as much as he had.

Jess looked up from his book. "You done over there?"

"I am."

Dean caught his ball and looked over at the dining set. "That looks great, Luke."

"Thank you, Dean." Luke yawned. "I'm beat. You guys wore me out today, dragging me all over the city like that. I'm not used to this."

Jess raised an eyebrow. "Uh, we weren't exactly the ones doing the dragging, Luke."

Luke laughed. "My mistake, nephew. So, the apartment looks good, huh? I think it feels a lot homier now. What do you guys think?"

"Definitely homier." Dean agreed. "Thanks again for everything you bought me today, Luke. I really appreciate it. I can't even tell you how much."

"I was happy to do it, Dean. I want you to have what you need. And I had a lot of fun with you guys today. Is there anything else either of you can think of that you need before I go?"

Dean's stomach growled loudly, making Jess laugh. "Uh, I'd say Dean needs dinner."

"Oh, jeez, we never even stopped for lunch!" Luke realized the day had gotten away from him and he hadn't thought about eating since their late breakfast, and neither boy had complained, so lunch had been forgotten. "I'm sorry about that. I can go whip you guys up something before I take off." Luke started to get to his feet.

"Oh, no, it's fine, Luke. I can do it." Dean stood up quickly, eager to be useful on a day when so much had already been about Luke doing things for him.

"Let's get takeout." Jess suggested. "I'll treat you guys. There's this really good taco place down the street that I want you to try, Luke. I think you'll really like it."

"Ok, whatever you guys want to do is fine with me. But, I want to pay for it-"

"Luke, stop." Jess said in his sternest voice. "I want to get it. You're my guest and you already did enough for me today. OK? I can buy my uncle a couple of tacos without going broke." Jess started to stand up. "I'll run out and pick them up and we can test out the new table. How's that sound?"

Luke didn't see a need for Jess to treat him to dinner, but he didn't want to make a fuss about it, and he figured tacos couldn't be that expensive. "Ok, whatever you want, Jess." Just then Luke realized that he still hadn't brought up the subject of him and Lorelai. And he was running out of time. "Hey, uh, Dean, would you mind going to pick up the food instead? I kind of need to talk to Jess about something before I go."

"Uh, yeah, of course." Dean readily agreed. "I'd be happy to." Before Dean could start to feel awkward about whether he should wait for someone to offer him cash or whether he should use his debit card and drain the meager resources left in his bank account, Jess was pressing money into his hand, telling him the name of the restaurant and which tacos to order.

Jess watched Dean get bundled up and leave the apartment.

"Hey, Jess. Can you come over here for a minute?" Luke gestured toward the table and chairs.

Jess turned toward Luke. He had been half-expecting this all day, but he still wasn't looking forward to it. Luke hadn't seriously reprimanded him for anything since he had left Stars Hollow the second time after returning from California, and he knew at nineteen it would be even more embarrassing now. He walked slowly over to the table and took a seat. Luke pulled out the other folding chair and sat down across from him. This was something new. Jess remembered being seated at the table in Luke's apartment with his uncle on his feet pacing around, laying into him about whatever he'd done wrong. Jess took this as a promising sign that this might be more of a conversation among equals as opposed to a parent scolding a child. Still, he wanted to get it over with, especially before Dean came back.

"So, I get that you're pissed, Luke. If I cut to the chase and say I won't do it again, can we please be done here?"

Luke looked confused. "What are you talking about, Jess? You won't do what again?"

Jess studied Luke's face. "This is about Lorelai, right?"

"Uh, yeah." Luke felt baffled and wondered if he'd been more obvious than he thought. "But, how did you know that?"

It was Jess' turn to be confused. "I mean, you got pretty pissed when it happened. So, I put two and two together…came up with four, you know how it goes."

"I got pissed?"

Jess sighed. Luke wasn't usually this obtuse. "Yeah, this morning? When Dean said not liking Lorelai was like not liking the circus and I listed her similarities to a circus clown. That's what this is about, right? You got pissed and yelled at me, but then you felt bad for yelling, and now you want to talk about it and calmly and rationally tell me what an ass I am, right? Before you really lay into me, though, may I please point out that attention-whore is just an expression for someone who thrives on attention, not a reference to someone who actually takes money for sexual acts. Just so we're on the same page before you start."

"Jess, I know what an attention-whore is. This isn't about that. Well, not really."

"I already said I was sorry this morning."

"I know you did, Jess. And I appreciate that. I didn't want to talk about that. I just wanted to tell you that Lorelai and I have started…seeing each other."

"You're dating Lorelai?"

"Yes, we're dating."

"Oh, well, uh, congratulations, I guess. I know you've been into her for a long time."

"Yeah, I have been. I think you might have picked up on that before I did."

"Well, I am an astute observer of people. And, you're, well, you." Jess looked away for a moment. "So, when did you finally ask her out?"

Luke smiled. "About a month ago, but I wanted to wait to tell you in person. And, I guess to make sure she didn't change her mind right away or anything." Luke laughed, but it sounded off to Jess, like he was nervous.

Jess nodded. He knew he should say something to the effect of whatever made Luke happy made him happy, but part of him felt like a sullen child who didn't want to share his parent with anyone, especially someone he didn't like and who had made no secret of not liking him back.

Luke took Jess' silence as a bad sign and proceeded cautiously. "And, I know you two don't really get along that well. And I'm not expecting that to change overnight, or anything, just because we're dating now…but, well, I love you, Jess. So much. And I really like Lorelai. I think I might already love her. And things are going really well with us, so far…And I don't want my being with her to come between you and me, because you are so important to me, Jess, and I always want you in my life. I just…I guess what I'm trying to say is that I really want you to be ok with this."

Jess took a moment to let the news sink in, his face expressionless. "Ok."

"Ok?"

"Yeah, I'm ok with it." Jess nodded, not sure if he was convincing himself or his uncle.

"Yeah?"

"Of course. I'm ok with whatever makes you happy. And you do seem happy. You seem really good. Granted, up until right now, I thought you were happy because you were here spending time with your favorite nephew, but hey…" Jess shrugged nonchalantly and forced a smirk onto his face.

Luke smiled warmly at his nephew. "Spending time with you does make me happy, nephew. Always."

Jess nodded. "Ok. So, we're good. We'll continue to be good. This won't change anything." Even as Jess spoke, he felt a seed of worry planting itself in his gut, knowing that this might actually change everything. He wondered if his uncle would still have time to spend just the two of them, or if he would be as available for his phone calls. Or, if his visits to Stars Hollow would be tense with Lorelai, and probably Rory, in the picture. He knew it was a childish thought, but he had gone most of his life without being anyone's top priority, and now that he had found a situation where he was loved like that, he didn't feel ready to give up the top spot in Luke's life.

"That's good to hear, Jess. I really love you, kid."

Jess nodded slightly. "I know. I love you, too."

"And I'm sorry you spent the day thinking I was going to come down on you about what you said this morning."

"It's ok. It was still a really good day. Having you here and everything. Plus, I figured after everything you did for me today, I owed it to you to sit through a lecture if you felt like giving me one."

Luke laughed softly. "Yeah? I'm not really sure how that works now. I felt like I might have overstepped earlier when I raised my voice at you. I'm not sure what the protocol is for reprimanding your adult nephew when you're a guest in his home."

Jess feigned concentration while he considered this. "I'm pretty sure it's still allowed if said nephew is being an ass and insulting your girlfriend."

"Huh. Good to know. You weren't an ass, though. You know, I actually think you mostly pick at Lorelai out of habit."

"Oh, is that right?"

"Yep. I think you two have a lot in common, and if you ever gave each other a chance and got to know each other better, you might just learn to like each other." Luke laughed at Jess' exaggerated expression of disbelief. "Hey, stranger things have happened, my friend. A year ago, you would never have believed that you'd end up friends with Dean, right?"

Jess thought that over for a moment. "Yeah, I can't argue with that. How about if I promise that if I ever come across Lorelai foraging through a dumpster, I'll let her sleep on my floor, too? She'd have to share the roll up mattress with Dean, though, but that goes without saying."

Luke smiled at his nephew. "That's a start."


	6. Chapter 6 - Luke's Visit - Part II

**Chapter 6 Notes:** Here's the second part of Luke's time in NYC. I felt like there were still a few things he had to do there. Thank you to everyone who is reading this story and especially to those who have taken the time to leave me reviews. I very much appreciate every word you give me.

 **Disclaimer:** I own nothing except my own obsession with Gilmore Girls.

 **Trigger Warning:** Homelessness. Mentions of death and loss.

"Chips and salsa?"

"Uh…" Dean knew this shouldn't be so stressful, and the anxiety he felt at the question added a new level of shame to picking up dinner with someone else's money. He had already placed the order that Jess had specified, one carnitas taco, crispy chicken taco and fish taco each for Jess and Luke and then whatever Dean wanted. Jess said he usually ate three tacos, but Dean could get as many as he wanted for himself. Dean normally, with normal being the time when he had had a job and spending money and parents, would have eaten about four or five tacos, but there was no way that he was going to order more than Jess when Jess was the one paying for dinner, so he had duplicated Jess' order for himself, too. That made nine tacos in all at $2.69 each. The electronic display on the cash register was at $24.21 before tax. Jess had given him two twenties. But, Jess hadn't mentioned anything about chips and salsa, which Dean could see from the menu on the wall behind the counter was another $1.99. Dean felt panicked. He didn't think anyone ever got Mexican takeout without getting chips and salsa. Certainly, he never had. It would be like having a burger with no fries. And he didn't want to show up without the chips if Jess was expecting them and had thought getting them was so obvious that it went without saying when he had given Dean instructions. But, he also didn't want to bring back something extra that hadn't been requested and risk appearing too comfortable spending Jess' money. He didn't want Jess to see him as even more of a mooch than he already did. Dean had walked into this little hole in the wall restaurant feeling ravenous from having gone without lunch, but now he felt a ball of stress lodging in the pit of his stomach, smothering his appetite. He no longer cared about whether he got to eat the chips and salsa or not, he just wanted to make the right decision and not aggravate Jess or appear presumptuous.

"You want chips and salsa with that?" The man working the register repeated his question a little louder, looking slightly impatient.

"No, uh, sorry. No, thank you." Dean finally answered, wanting to err on the side of conserving Jess' money. If Jess asked about it, Dean could simply say he forgot the chips. Being forgetful had to look better than being greedy.

The man totaled the order and Dean handed him Jess' money.

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It was only a little after six o'clock, but it felt much later after such a full day. Dean walked through the dark, his body hunched forward, braced against the cold and wind, one gloved hand gripping the takeout bag, the other shoved into a coat pocket. As he walked toward Jess' apartment, he passed the line of men forming at St. Sebastian's and felt a twinge in his gut as he got a glimpse of what he must have looked like to Jess when he had stumbled upon him that night in the alley. Physically unkempt, scared, and vacant-eyed. Hopeless and broken.

He remembered those nights in the shelter as some of the worst of his life, second only to the night his parents died and the weeks immediately following the accident. He could still remember lying on a cot, shivering under a thin blanket even with all his layers on, his body curled protectively around his backpack, keeping close to the only things he had left. Avoiding eye contact with everyone, but too frightened to actually close his eyes. Trying to block out all the noise around him. Someone mumbling quietly to himself, someone else talking erratically, sounding crazy, the occasional startling scream during a nightmare, someone sobbing, always someone sobbing, and on the worst night, loud aggressive words that resulted in an attempted stabbing, a visit from the police, and a completely sleepless night for Dean.

He thought about the days in between those nights, and how his world had become so small, narrowing in width over time from a normal existence to one focused solely on survival. He remembered renting rooms at cheap motels at first. Showering and heading out to job hunt all day, every day, knowing that getting a job before he ran out of money had to be his top priority. He had even tried to connect with friends from Stars Hollow at first, before things had gotten so bad, reaching out to Kyle only to be told by his mom that he was somewhere in the Middle East with the Navy and to Chad, who Dean had gotten on the phone but chosen not to burden with his own problems after learning Chad had gotten his girlfriend pregnant and was freaking out about how to handle it. After almost a month of not being able to find a job, Dean's savings had dwindled to the point that he could no longer afford to rent a room, or even keep his clothes clean and presentable. Not if he wanted to eat, too. He thought he had been scared before, but pure panic had kicked in then. The response he had received as he applied for jobs became colder as his appearance deteriorated and his desperation become palpable. He had slid into a real depression then, as each day became focused on getting three basic needs met: staying fed, staying warm, and getting to the shelter in time to get a bed for the night.

Dean felt the familiar panic rising in his chest and swirling around in his head. He started to feel lightheaded. This past week with Jess, and especially today with Luke and the shopping trip, had allowed Dean to push down some of the panic that used to overcome him daily when he had been alone and on the street. But, seeing the men in line for the shelter brought all Dean's fears and anxiety surging back up. He knew that none of his issues had really been resolved. Not in any way that was substantial or lasting. He still had no job, no money, no way to meet his own needs without relying on Jess', and now Luke's generosity. He still broke out in a sweat over whether to spend $1.99 on chips and salsa. He was so grateful to be allowed to stay with Jess, but he was keenly aware of how quickly and easily he could end up standing in that line again. He knew he needed to take advantage of this period of respite to get himself back on his feet and try to move forward with his life. Get a job. Save up some money. Reestablish contact with Clara. Get himself in a position to take care of himself. It all felt so overwhelming. He ducked his head as he ploughed on through the cold, trying to control the panic before it consumed him.

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Dean struggled with the key in the lock. He could feel his hand shaking slightly, enough to make him clumsy. He just needed to keep it together until Luke left and Jess went to bed. Just a few more hours. He could do that. When he got the door open and let himself in, Jess and Luke were seated at the new table and looking toward him curiously.

"You ok out there? I was starting to think someone was trying to break in?" Jess said, a small smile on his face.

Dean nodded without making eye contact. "Yeah, sorry, my key was…being weird, I guess."

"Thanks for going out to pick up the food, Dean." Luke said.

Dean nodded again. "No problem."

Jess looked at Dean thoughtfully before he got up from his chair and walked over to the kitchen area. "Are you guys good with water, or do you want something else? Today we have several options. We've got tea, orange juice, cranberry juice and a carton of chocolate milk that made its way into the shopping cart when Luke wasn't looking."

Luke chuckled. "I did see that, you know. Just because I didn't say anything doesn't mean I didn't see you do it. I saw the box of Cinnamon Toast Crunch, too."

Jess shrugged as he pulled three glasses out of the cabinet. "It goes so well with chocolate milk. How could I resist?"

"You're a five-year-old." Luke shook his head, a smile slowly spreading on his face as recognition hit. "Hey, you know who you remind me of right now?"

Jess looked over at his uncle, a mock scowl on his face. "Do not say what I think you're going to say."

Luke laughed.

"I mean it." Jess added.

Luke kept smiling, enjoying his nephew's annoyance. "I like that you knew who I was talking about without me having to tell you."

"Ugh, stop. So, what do you want to drink?"

"I'm fine with just water."

"What about you, Dean?" Jess turned to Dean, who had set the takeout bag down on the table and was slowly unwinding his scarf.

"Uh, yeah. Yeah, water's fine, Jess. Thanks."

Dean didn't like the careful look Jess was giving him, as if he was analyzing him for some new detail that hadn't been there when Dean had left. "You ok, Dean?"

"Yeah, yeah, I'm good, Jess."

Jess nodded slowly. He filled the last glass with water, grabbed a few napkins, and carried everything over to the table.

"Oh, uh, here, Jess. I have your change." Dean pulled Jess' money out of his jacket pocket and held it out.

"Thanks. You can just leave it on the counter. You guys take the chairs since you're my guests and I'm a seasoned veteran at eating tacos on the floor without making a mess."

"Oh, no, Jess, really-"

"Yes, Dean, really. I insist."

"Ok, I, uh, I'm just gonna wash my hands." Dean walked over to the kitchen sink.

Jess set out a couple of napkins on the table in front of Luke and placed one of each kind of taco on them. After checking that Dean had ordered the same thing for himself, he set up Dean's meal on the other side of the table. "Oh, crap. I forgot to ask you to get chips and salsa, too. Sorry about that."

"No plates, huh? This is how you eat?" Luke asked.

"Plates defeat the whole purpose of takeout. Be happy you even got a glass."

Luke nodded, knowingly. "Right. Because then you'd have to wash the plates after, and that's way too much effort."

"Hey, you got it in one!" Jess picked up one of the waters and the bag with the three remaining tacos and walked over to sit on the edge of his mattress.

Luke smiled. "You know, I think I've heard that very same philosophy before. From someone we all know…"

"Stop."

"I'm serious, Jess. You two have a lot in common. That's all I'm saying."

"Stop that. I'm trying to eat over here."

"Like two peas in a pod." Luke laughed at the childish scowl on his nephew's face. "Hey, I'm just sayin…"

Jess took a bite out of his first taco, refusing to humor his uncle.

"Hey, Dean, are you ok?" Luke asked.

Jess noticed the worried look suddenly on his uncle's face, and turned to see Dean, standing at the sink, his hands braced on the counter on either side, leaning slightly forward. In the silence that followed, Jess could hear Dean's breathing, quick and shallow. "Dean?"

Luke was already on his feet and approaching Dean slowly, placing one hand gently on the boy's back. "Dean, hey. What's going on? You ok?"

Dean shook his head from side to side, wordlessly. A tear escaped from his eye and ran down his face. He couldn't talk. He could barely breathe, and he needed to focus on that first. He head was swimming. He felt light and dizzy. He was sweating profusely. A disorienting wave of nausea hit him, and he knew he needed to get down on the floor. That usually helped ground him when this happened. Gripping the edge of the counter for support, he slowly lowered himself to his knees. He put his hands on the floor in front of him and leaned forward, lowering his forehead to rest on the cold tile floor. If he could just focus on breathing, on moving air in and out through his nose, he would be ok. He had been through this enough times to know that this helpless, out of control feeling would eventually pass. And that he would live through it. He always had before. Even the times he hadn't particularly wanted to. For now, he just had to concentrate on breathing.

He felt Luke beside him on the floor, rubbing his back, and he remembered his surroundings. He felt a surge of shame at how much he was humiliating himself right now. He felt two more tears run down his face. He heard Luke talking to him in a soothing voice, like the one his mom had used when he was little and had fallen off his bike and broken his arm, but she hadn't wanted to scare him and had sat in the backseat with him, holding him and telling him that he was ok, that he was her brave little boy and that everything was going to be just fine, as his dad drove them to the hospital. Dean felt a sharp stabbing pain in his chest at the memory. The tears started in earnest then. He knew it was a pathetic thought, but he really wanted his mom right now.

Jess was still sitting on his mattress, a taco frozen in one hand, staring as his uncle comforted Dean, whose body was shuddering with sobs as he remained kneeling, head on the floor, in what looked like a sloppy version of a prayer position. He was still in shock at the transition to the current situation when Dean had seemed ok just a few minutes ago. He listened to his uncle doing his best to calm Dean down and the main thought running though his head was how grateful he was that Luke was still here for this.

"You're ok, Dean." Luke's voice was gentle, but Jess took in the worried look on his face. He had only seen that look a handful of times before, and always aimed at him. The moment felt surreal. Jess started to feel his own eyes dampen in sympathy for Dean's distress, and he quickly blinked away the wetness.

"Let it out if you need to. You're going to be all right, kid." Luke was petting circles on Dean's back with the palm of his hand. "We're here, Dean. You're not alone. Everything is going to be ok."

Dean had no sense of how much time had gone by like that, but eventually it passed. Like it always did. His tears slowed and finally stopped. He could feel his breath moving easily through his windpipe again, like normal. He slowly lifted his head and chest and sat back on his heels. He was staring at the floor in front of his knees, afraid of looking up and meeting any judging eyes. Like always, he felt exhausted, completely spent, physically and emotionally. Like he could crawl over to his nest of blankets and pass out for the night. Shame at his inability to control himself always accompanied a panic attack, but, this time the shame was intensified at having had an audience to his dramatic display of weakness.

"Jess, can you bring me a glass of water, please?" Luke kept one hand on Dean, gently massaging the boy's shoulder, as he looked toward his nephew. "Jess, seriously." Luke scolded. "Have you really been sitting there eating a taco all this time?"

"What?" Jess snapped out of his thoughts and looked down in surprise to see the taco he was holding, one bite removed, feeling like it had somehow betrayed him by still being in his hand during this crisis. "No, I, uh…"

"Just get the water, Jess."

Jess set his taco back in the bag and scrambled to his feet, quickly grabbing Dean's water and bringing it over to Luke.

"Thanks." Luke took the glass and held it out to Dean. "Hey, Dean. Do you think you can take a sip?"

Dean looked at Luke then, a quick glance taking in Luke's concern. He took the glass of water and lifted it to his mouth, taking a long drink. He felt dehydrated after crying so much. When he was done, he lowered the almost empty glass and focused his gaze on it as he held it in both hands at his lap. "Thanks. I'm, uh…I'm really sorry about that."

Luke's palm was cupping the back of Dean's neck. "Hey, listen to me, Dean. You have nothing to be sorry about, ok? This stuff happens sometimes. We've all been there. It's ok. No one's judging you. You know that, right?"

The care in Luke's voice was too much for Dean to take. He could feel his eyes start to fill again. Not with the out of control sobbing and convulsing like before, but enough that he was embarrassed to look up. He nodded a response to Luke, eyes still downcast.

Luke sighed. "Dean, c'mere, kid." He took the glass from Dean and set it to one side on the floor and pulled Dean into a hug. Hugging Dean was an entirely different experience from hugging his nephew. Dean's response was immediate, closing the gap between them completely, holding onto Luke with an intensity Jess had never shown and pressing his face in Luke's shoulder. Luke reflected on the comparison. Jess tolerated hugs because he loved Luke and knew that being able to hug his nephew made him happy, but this right here was a kid who desperately needed a hug, and had for who knows how long. He cupped the back of Dean's head with one hand, and waited a few beats, just as he did with Jess, making sure to let the boy be the one to pull back first.

Dean sat down on the floor and leaned back against the cabinets under the sink, letting them support his weight. He wiped at his eyes with the back of his sleeve, trying to dry his tears. He looked at Luke, still on his knees in front of him, a warm and worried expression on his face, and Jess, still standing a couple of feet behind his uncle, as if frozen in the spot where Luke had taken the water from him, a matching worried look on his face. Dean started to laugh softly, almost silently, his total exhaustion bordering on delirium. Luke's expression changed from concern to puzzlement, before a small smile spread on his face. "What's so funny?"

Dean shrugged one shoulder slightly, still too wiped out for much movement. "Nothing. I don't know. It just hit me how weird this all is…I mean, a year ago, Jess and I couldn't even be in the same room without being jerks to each other. Two years ago, you pretty much hated me for breaking up with Rory…"

"What? Don't be silly. I never hated you, Dean."

Dean laughed. "It sure felt like you did that time you had me in a headlock outside the diner when I tried to talk to Rory."

Luke felt a rush of embarrassment at the memory. "Oh, that. I'm sorry about that, Dean. Really. I just get over protective of Rory sometimes. And I kind of lost my mind a little. It wasn't anything personal, honestly."

"Um, what now?" Jess said. "Someone definitely needs to tell me that story."

Dean laughed. "It wasn't as bad as it sounds. It's just so crazy that now I'm sleeping on your floor in New York City and Luke just bought me underwear and helped me through a panic attack." Dean wiped away another tear as it started to escape from his eye. "And, don't get me wrong, I'm so grateful for all of it. To both of you. It just feels kind of…unreal, I guess."

Jess nodded. "I get what you're saying. It does feel pretty weird sometimes when I think about it. Like, I wonder what Rory thought when she heard that we're living together now, and that we're friends. For her to just hear that from Lorelai and not be able to see how we are now. It's got to be weird to process. I picture her head exploding when she tried to reconcile this new fact with how she remembers us acting around each other."

Dean looked thoughtful. "Yeah, I'm sure she's pretty confused by it."

"Rory doesn't know." Luke said. "I asked Lorelai not to tell her until I came out here and got to talk to you, Dean. I wasn't sure what you wanted people to know."

Dean and Jess exchanged looks and simultaneously cracked up laughing.

"Thanks, Luke. I appreciate the thought." Dean said, a smile still on his face.

Luke looked confused. "What? What's so funny, now?"

Jess addressed Dean. "I'll explain it to him. Luke can be a little dense sometimes. And by a little, I mean a very thick fog. I'm talking pea soup here-"

"Jess…" Luke warned.

Jess laughed. "Sorry, Luke. Rory knows about Dean."

"How would she know? I asked Lorelai not to tell her."

Jess laughed again. Dean chuckled but stopped himself quickly at the annoyed expression on Luke's face. "Oh, sorry. You were being serious."

"That's so cute, Luke. Really." Jess said, patting his uncle on the arm. "I feel like buying you a pet unicorn right now. Let me help you out with some life advice here. You and Lorelai will never have a secret from Rory. Never. As in, not ever. There is no fact known by Lorelai or Rory that is not known by both. They will have many secrets from you, but you and Lorelai will never have a secret from Rory. They tell each other everything including all your personal shit. If you snore. Rory knows. If you say something to piss off Lorelai. Rory knows. If you mess up in any way. Rory knows. You following what I'm saying here?"

Luke looked annoyed and Dean looked confused. Jess filled him in on what he had missed. "Oh, yeah, Luke is dating Lorelai now. That's what he wanted to tell me when he sent you off to fetch the tacos."

"Really? That's great, Luke! I'm really happy for you." Dean grinned at Luke. "And don't let Jess freak you out. We were both on the other side of that situation when we dated Rory. Maybe Lorelai doesn't tell Rory as much personal stuff as Rory tells her." Jess caught Dean's eye again and started giggling quietly. Dean tried not to join in out of respect for Luke's feelings. "Jess, c'mon, we don't really know how much Lorelai tells Rory?" Jess kept giggling. "Jess." Dean tried one more time but the giggling became contagious and he found himself laughing against his will.

Luke was smiling warmly at them, a smile that brought Dean back to the ones his own father used to direct at him and Clara when he had been indulging one of them in some fit of silliness, pleased to see his child happy and laughing even if he didn't really understand or approve of the reason for it. A dad smile.

Luke slowly rose to his feet. "All right. You two clowns yuck it up over here. Laugh your little hearts out at what a sucker I am. I'm going to go eat dinner before it gets too cold."

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"Well, I had a really great time with you two today. Thanks for having me over." Luke was standing by the door, his jacket on, ready to hit the road.

"Thanks for coming, Luke." Jess felt sadder than he had expected at seeing Luke leave. Today had been a really good day. He felt childish for having the thought, but sometimes he missed living with his uncle. He knew he hadn't fully appreciated the feeling of being loved and taken care of when he had lived with him. He had wasted too much time fighting against it while he had processed his new family dynamic. But on days like today, he was reminded of what he still had, and now he was mature enough to realize how lucky he was. "And thanks for the table and the food and everything you did today. I really appreciate it."

"Me too, Luke. Thanks so much for everything." Dean said.

"You're both very welcome. It was my pleasure."

"And as soon as I get a job, I'll start paying you back for everything you bought me today. I promise." Dean added.

"Dean." Luke said with a smile. "We've been over this so many times that I'm not going to dignify that comment with a response."

Dean nodded, a small smile on his lips. "Ok. Thanks, Luke. I just want you to know how grateful I am. For the stuff you bought me. And for…everything. Really."

"I know you are, Dean. And I'm just as grateful that you let me do it." Luke said. "All right, it's getting late. I should really hit the road." He took a step toward Jess and pulled the boy in for a hug. "I'm going to miss you, kid." He felt Jess' movement against him as the boy nodded his head in agreement.

"Me too, Luke."

Luke planted a kiss on the top of his nephew's head before the boy pulled back. "I love you, Jess."

"I know. I love you, too."

Dean had taken a step back to give Jess and Luke space while they said their goodbyes. Luke turned to him now, with one arm out. "Get over here, Dean. I picked out your underwear today. I'm pretty sure that puts us on hugging terms now." Dean laughed and took a step toward Luke, letting himself be pulled into a hug. Despite the panic attack, it had been a good day. Possibly Dean's best day in a while, and he was sad it was ending.

"Ok." Luke pulled on his hat and gloves. "You guys call me if you need anything, ok?"

Dean nodded, while Jess said. "I don't think either of us are going to need anything for a long time after today. I think we're all set for a while."

"Good. Then I did my job." Luke smiled as he opened the apartment door. "Don't be strangers. Come visit me in Stars Hollow sometime soon, ok?"

Both boys nodded.

"All right. Be safe. You two take care of each other."

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Luke started his truck and pulled into the street. The only thing he hated more than driving into the city in the daylight was driving out of it in the dark. But it was worth it to have gotten to spend more time with his nephew. Whenever Luke left Jess in New York, it was with a heart heavy with the knowledge that this may be the closest to each other that he and Jess ever live again. The boy could easily move further away in the future. For a job or a girl. Who knew. He was still so young and unsettled. Luke missed having him nearby, in his apartment, in the diner, where he could easily check up on him whenever he wanted. He missed the boy's presence in his daily life immensely. But, tonight, leaving Jess felt a little easier to take than usual, knowing that Jess had Dean with him for company, and that Luke himself was returning to Lorelai in Stars Hollow. It made the loss feel a little more bearable. Life moved on. Children grew up and moved away. That's how it went. At least for the time being neither of them was alone. Luke was on the highway before he realized that he had spent the day so preoccupied with the practical ways he wanted to help Dean that he never really talked to the boy about his situation. Luke sighed. He was leaving New York not knowing much more than he had when he arrived.


	7. Chapter 7 - A Little More Conversation

**Chapter 7 Notes:** Here's a little conversation between Jess and Dean on the night of Luke's visit. There is a brief mention of something that happened on Jess' last visit to Stars Hollow that may not have happened in cannon at this point yet. I'm really not sure, but I'm bending the Stars Hollow timeline to fit my needs while hopefully keeping the spirit of what happened intact. Thank you to all who had read this story and left me reviews. All feedback is warmly welcomed.

 **Disclaimer:** I own nothing except my own obsession with Gilmore Girls.

 **Trigger Warning:** Mentions of death and loss.

Dean lay on Luke's camping mattress, which was more comfortable than he had expected, outfitted with brand new sheets and a pillow. He had expected to pass out as soon as he laid down. He was physically exhausted from the long day of shopping and the panic attack. But he found himself wide awake as he listened to the sound of water running as Jess got ready for bed in the bathroom. He knew how fortunate he was that Jess had stumbled across him in the alley that night, and he felt extremely grateful for the roof Jess was currently putting over his head and for everything Luke had bought him and done for him today. He felt like things were coming together to make him feel like he really could be ok again. That he could get a job, connect with people, maybe have a normal life again one day. But, an important piece of his life was still in desperate need of fixing. Clara, the most important piece. Every time he thought about her, he felt a wave of worthlessness overwhelm him at how he had abandoned her. It had gotten to the point where it was easier to push down thoughts of his sister altogether, and that left Dean feeling deeply ashamed of himself.

He had been too embarrassed about what happened and too scared of running into his uncle or cousin to try to make contact with her for weeks after he had been thrown out. The only time he had called the house was almost a month after he had left, from a dingy motel room when his money was starting to run out and he hadn't known what to do. He had called the house phone at three o'clock one afternoon, hoping to catch Clara home from school, but before his uncle had come home from work. But, his uncle had picked up. Dean had been caught off guard and listened wordlessly as his uncle repeated the word hello, three times in a row, the annoyance in his voice escalating each time, before he startled Dean by slamming the phone down. Dean hadn't called back. He had fallen into a downward spiral after that, fixated on his own weakness and worthlessness, taking every job rejection or other set-back as further validation of how pathetic he was. The depression hadn't started to lift until he had connected with Jess, but now that it had, he knew he couldn't let himself fall into that headspace again. It had only made things worse. He promised himself he would fix this and make things right. He needed to. Nothing would really feel right until he had Clara back in his life. If his aunt and uncle didn't want him in their house, that was fine. He'd get a job and take care of himself. But, they couldn't keep him from Clara. He was her brother. He had the right to see her. He could live with them hating him forever, but he couldn't go on this way, with no contact with his sister. It wasn't right. It hurt thinking about how much he missed his little sister, and it hurt even more to think about how much it had to be hurting her and how disappointed his parents would be that he hadn't been there for Clara the past couple of months. He resolved to make things right, and to start by trying to get in touch with Clara again tomorrow.

The bathroom door opened and Dean wiped at the dampness that had formed in his eyes as Jess walked into the room. He made a second resolution to himself, to stop crying. He had been doing far too much crying lately and it was getting embarrassing. He needed to be stronger going forward. For himself and for Clara. And for the first time in a long time, he felt like he could do it. This week, and especially today, felt like a kind of turning point to Dean, breaking down the last couple of months of his life into before and after, with 'before' being Dean as a depressed mess, living on the streets and feeling sorry for himself. But, 'after'…'after' he would be stronger, better. He would get his shit together. He felt lighter and hopeful for the first time in a long time.

Jess turned off the light and then froze mid-step toward his mattress. "Oh, uh, sorry, did you still need the light?" He still hadn't become entirely accustomed to having to accommodate someone else in his space, but he didn't want to be inconsiderate to his guest. Or roommate. He wasn't exactly sure how to classify Dean's status in his apartment any more, since it didn't seem like Dean was going anywhere anytime soon.

"No, I'm good. But, thanks for checking." Dean turned toward Jess as his eyes adjusted to the dark, waiting for him to climb into bed. "Hey, Jess. I just really want to thank you for today. It was great. It was the best day I've had in ages."

Jess reflected on that a moment. "Yeah, it was a pretty good day. But, it was all Luke. You don't need to thank me for it."

Dean rolled onto his side, facing Jess in the dark, his head propped on one bent arm. "Yeah, I do. I know Luke paid for everything, and I'm so grateful to him for that, too. But, he's your family, and I want to thank you for sharing him with me today. I know you told Luke about me because you knew I needed help. And you let me hang out with you guys all day and basically crash your visit with him. And I want you to know how much I appreciate that. Today felt really…normal, I guess. And, normal feels really good right now. I'm starting to feel like I might actually be capable of getting my shit together and having a normal life again someday."

Jess thought about that for a moment but wasn't sure how to address the last statement. He wanted to tell Dean that of course he could get his shit together and have a normal life, but he wasn't sure he could make it sound convincing when he shared the very same concern about his own life. And all he had to overcome on the road to normalcy was some poor parenting and having flunked out of high school. Nothing like what Dean was going through. He settled on focusing on today. "It was good having you along today. I had fun. And your presence gave Luke someone other than me to focus all his overbearing parental energy on for a change. Hey, maybe I should be the one thanking you!"

Dean huffed out a soft laugh. He couldn't see Jess' face in the dark, but he could hear the smirk in his voice. "He is very parental, isn't he?"

"He is that." Jess agreed. "But, he means well. Always. I hope he didn't drive you too crazy."

"Huh? No, I meant with you. It was funny to see you guys together. Like, how you act with him and everything."

"What are you talking about?" Jess asked, puzzled. "What's so funny about how I act with him?"

"I don't mean anything bad. You're just different than I expected with him, I guess. But, it works. You guys are cute together, you know?"

"Oh, so now I'm funny _and_ cute?" Jess smirked. "Wow, it's like you want to sleep on the fire-escape tonight." Jess threatened with no heat, trying to figure out what Dean was getting at.

Dean laughed. "No, I'm not saying this right. It's like, you came to Stars Hollow with this real attitude toward authority figures, right? Toward pretty much everyone really. I've seen you be a complete dick to teachers more times than I can count."

"Only when they deserved it for being dicks to me."

"And Principal Merton-"

"That jerk always deserved it." Jess defended himself. "He was out to get me from the second he met me."

Dean laughed again. "It's just, I had this image of you as being this sarcastic, cocky little punk. You weren't afraid of getting in trouble at school. You didn't care who you pissed off. It just seemed like you didn't give a shit what anyone thought about you. And, then seeing you with Luke. You were different. It was cute."

"Please stop calling me cute. It's making me even more uncomfortable than all your gratuitous thanks."

Dean smiled. "Sorry, it's just, you guys are way more parent-child together than I pictured. I kind of assumed you had been giving him the same attitude you gave everyone else when you lived with him. I remember feeling sorry for the guy after I got to know you, that he had to live with you. I pictured you giving him all kinds of attitude all the time, never doing what he told you to, and just generally driving him crazy, you know, like you did with all the teachers at school. But, instead, he totally treats you like you're his kid and you turn into this good little boy around him. It's funny to watch."

"I do not turn into a good little boy around him!" Jess squawked indignantly. "You are so full of shit right now, Forrester!" Jess couldn't gage how offended he should be by this description. Dean didn't seem to mean it as an insult, but still.

Dean giggled. "Not in a bad way. Just like, you respect him, and you care about what he thinks about you. It made me think about being with my dad." Dean paused for a moment, automatically tamping down memories of his own father before they could surface and drag him under. "Like, anytime you guys were arguing about something, like when Luke wanted to go to REI and you wanted to just get the thermals at Target since we were already there, or when he thought you needed a table to eat at and you didn't want one, you always ended up caving and going along with whatever Luke thought was best. And, when you were making fun of Lorelai and comparing her to a circus clown, which is even funnier in retrospect, by the way, knowing that Luke is dating her, and he shut you down with a." Dean deepened and slightly raised his voice in imitation of Luke. "Watch yourself, young man! He totally spanked you, and you were all." Here Dean went into a high falsetto. "I'm so sorry, Uncle Luke. I promise I'll never do it again." Dean was really cracking himself up now. "It's just not a way I could have pictured you acting with someone who had any authority over you before today. It was funny to see it. But nice. You guys seem really good together."

"Wow, less than a week into our new friendship and you're already turning on me like this?"

"Aww, you just called us friends, Jess! I knew I'd grow on you!" Dean smiled. "That right there is the cherry on top of this day for me."

"If I were you, I'll be a little less concerned with your funny jokes and a little more concerned with sleeping with one eye open tonight. You seem to be a pretty deep sleeper. I'd hate for you to wake up out on the fire-escape with no memory of how your stupid, gigantic ass got there." Jess said. "And for the record, Luke has never once called me young man. Even he's not that lame."

Dean laughed again, letting it peter off into quiet giggling before subsiding completely. For the first time he really wondered about Jess' family situation. He knew from Rory that Jess had moved to Stars Hollow to live with his uncle because things weren't good with his mom back in New York, but he didn't really know what that meant. And while Jess' relationship with Luke certainly seemed to be a good one, Dean knew there had to be a lot of hurt that went along with being rejected by your own mother. Sure, Jess had been pretty insufferable back in high school, but Dean couldn't picture his own mother kicking him out over anything, no matter what he had done or how badly he behaved.

A few minutes later, Dean broke the silence. "Hey, Jess? Can I ask you a question?"

Jess gave a noncommittal grunt in response, half muffled by his pillow.

"How come you lived with Luke in high school anyway?"

Jess sighed. He was tired and wanted to go to sleep. He thought about reminding Dean that he had to get up for work the next morning, but he didn't want to seem like a dick by inadvertently rubbing it in Dean's face that he had a job, when Dean didn't, or to seem like he was somehow holding it over Dean that he was the one who paid the bills.

"I mean, what happened to your parents?"

Jess gave up on trying to sleep and turned his head slightly toward Dean. "Hmm, well, I've always suspected they were dropped on their heads as small children."

"What?" Dean was caught off guard by Jess' sarcastic response.

"Nothing happened to my parents." Jess was surprised by the edge of hostility he heard in his own voice. "They're idiots. They happened to themselves."

When Dean didn't say anything, Jess started to feel bad about snapping, especially after Dean had already shared so much with him, telling him about his parents' death and what had transpired at his aunt and uncle's house to get him kicked out. He recalled something he'd read in the book Luke had forced on him the last time in had been in Stars Hollow. About how relationships were healthiest when there was a mutual and equal exchange of emotional intimacy. The book had been referring to romantic relationships, but he figured the same rules applied to friendships, especially new ones where the foundation was still being laid.

Jess sighed again. "My father was a chickenshit who left right after I was born because he couldn't deal with being my father. And I mean right after, like a couple of days after. As in, he went out for diapers and never came back. I didn't hear from him until the end of senior year. I ended up spending a couple of weeks with him and his girlfriend and her kid at their place in California, but I had to beg him to let me stay with him. He didn't really have room for me. In his house, or in his life. My mom was a pretty unstable person for most of my childhood. She drank a lot and did a lot of drugs, mostly pot, and she went through a lot of…phases, I guess you could call them, for lack of a better word. She was always into some crazy alternative shit that she was convinced would 'fix' her fucked up life. Meditation, astrology, macrobiotics, ayurveda, aligning her chakra's, following her spirit guide, then her spirit animal, then her own inner voice, something involving running a stick around the inside of metal pots to make this fucking annoying vibrating noise that I can't remember the name for. You name it she's tried it and none of it lasted and none of it made her any happier or any less batshit crazy. In addition to working toward personal enlightenment, she held a few random shitty jobs here and there and dated and married a lot of unsuitable men, most of whom also had difficulty holding down jobs, had drinking or drug problems of their own, and didn't really like me very much and weren't always shy about showing it. Then she kicked me out at seventeen and Luke took me in. The end."

Dean was quiet for a moment, sorry he had brought up the topic to begin with. "I'm sorry, Jess. I had no idea. That sounds like it must have sucked…"

"It did suck. A lot. But, you don't need to feel sorry for me. Really. Me not having my parents isn't like you not having yours. I get the impression yours are actually worth missing."

That hit Dean hard. The idea that Jess didn't have his parents in his life and didn't even miss them. That seemed even more depressing to Dean than his own situation. He couldn't imagine not missing his parents every single day, many, many times a day. "Jess…" Dean started cautiously, knowing what he would want in Jess' shoes, and wanting to be able to do something for Jess after everything he'd done for him. "Do you need a hug?"

Jess barked out a sharp laugh. "I'm good, thanks. I've lived with this shit my whole life. I'm used to it. And, it all turned out ok. Getting sent to live with Luke was the best thing that could have happened to me."

Dean was quiet, trying to process a mother so bad that being separated from her could be considered the best thing in her child's life. He regretted how harshly he had judged and treated Jess in high school. Dealing with his family situation couldn't have been easy. Even when Dean's father had had an affair and his parents were fighting all the time, Dean had never once believed that they didn't love him or that he couldn't depend on them to take care of him and want him around.

"Is your mom still in New York?"

"Yep."

"Do you ever see her?"

"I've seen her twice since I moved back to the city. Once on my own, and once when Luke was visiting and he made us meet up with her for lunch." Jess was starting to feel badly about how negatively he was depicting Liz. Not that anything he said wasn't true, but he didn't want to paint such a bleak picture. "I don't hate my mother, or anything. She's not a terrible person. She's just…someone who wasn't cut out to be someone's mother. I get that she did the best she could when I was a kid. But, the best she could…just, wasn't that great. And, I don't know, I just feel like I've been doing better without her as a regular part of my life the past few years. When I need a parent type person, like I did today, I go to Luke. I think I need to work through some stuff from my childhood on my own and it's easier for me to do that when I'm not wrapped up in her shit. Does that make sense?"

Dean nodded, then realized Jess probably couldn't see it in the dark. "Yeah, I think so. I just can't imagine being in the same city as my mom and not wanting to see her."

"Then she must have been a really good mom."

"She was. She was really great. Both my parents were." Dean's voice thickened as he choked up. "I miss them so much." Dean felt the confidence that had developed over the course of the day start to evaporate. He felt like he'd been kidding himself thinking things were about to get better. "I don't know how I'm ever really going to be ok again without them. It feels impossible sometimes."

Jess debated with himself for a moment before speaking. "I think you'll be ok again. Eventually. You know, I was, uh, really jealous of you when I first met you. And not just because you had Rory. You just seemed to have this perfect family. You were close enough to your dad that you guys built a car together. I'd see you stop by the diner after you got off at Doose's to say hi to Rory and Lorelai and then tell them you were heading home for dinner because your mom had made your favorite and saved you some. You had this little sister that you genuinely liked and took places with you. Everyone in town thought you were this great guy. You had friends and played on teams and teachers liked you. You had this whole perfect little life. I had never seen anything like it except on TV." Jess paused. "I'm really sorry you lost them, but you still have everything they gave you. I, uh, I spend a lot of time thinking about the normal stuff, the self-esteem and the emotional skills, that I didn't really develop growing up with my mom the way she was. Luke helped me a lot, to see myself differently and to be less angry about everything, but I know I still need to work on a lot of stuff to be able to have a decent life without always sabotaging myself because I don't believe I deserve anything good. But, you already have so much of that stuff, Dean. All the good things your parents raised you with. It might not feel like it right now, but I think you'll still be able to have a normal life and be a good person because of what they did for you when you had them and all the good stuff you learned from them. I think they probably gave you everything you need. And you didn't lose that when you lost them."

Dean was tearing up now. His emotions overwhelming him as he reflected on what he had received from his parents and what Jess hadn't. So much for his new no crying resolution. "Jess?"

"Yeah?"

"I really think I need to give you a hug now." Dean's voice wavered a little at the end, and he sniffled. "Is that ok?"

Jess felt a sudden jolt of anxiety at the idea of physical contact with Dean, but he didn't feel like he could say no without feeling like a jerk when Dean was expressing a need so directly. "Uh, I guess."

Jess had barely started to sit up in preparation, when Dean was kneeling over him in the dark, with his long arms wrapped snugly around Jess, holding his upper body slightly off the bed. Jess tried to return the hug, awkwardly winding his left arm around Dean, his hand landing lightly on his back, instinctively keeping his right arm free in case he needed to defend himself. Jess felt Dean's hair against his ear. It felt strange being this close to another man who wasn't Luke. Jess also felt vulnerable as he took in how much bigger Dean was than him, and how he was in a very defenseless position, practically underneath him. After a beat, Jess patted Dean's shoulder a couple of times with his right hand, effectively tapping out of the hug as he tried to signal that he needed to wrap this up. Dean took the hint and pulled back from Jess, retreating to his own mattress. He hoped the hug had helped at least a little. He knew Jess liked to act like nothing bothered him, but Dean didn't believe that Jess could tell him what he just had about his family without it making him sad on some level. "Thanks for letting me do that, Jess." Dean's voice sounded clearer now, more stable. "I know you don't like stuff like that. But, I really needed to do that."

"Sure." Jess responded, confused as to how Dean could have gotten anything positive out of that awkward experience. If they never hugged again, it would be ok with Jess.

"So…" Jess said. "If the late-night talking about our feelings portion of tonight's slumber party is over, can I go to sleep now?"

Dean smiled. "Yeah, you can. I'm sorry I'm such a mess. Thanks for putting up with me. You're a good friend, Jess."

Jess smirked, eager to lighten the moment. "I know."

Dean laughed. "Goodnight, Jess."

"Goodnight, Dean."


	8. Chapter 8 - Dean Gets His Shit Together

**Chapter 8 Notes:** Things start looking up for Dean. Jess has a chat with Dean, and then one with Luke. Thanks to everyone who is still reading and especially to those who have taken the time to leave me feedback. Your reviews make my day! :)

 **Disclaimer:** I own nothing except my own obsession with Gilmore Girls.

 **Trigger Warning:** Mentions of death and loss.

In the week following Luke's visit, Dean pounded the pavement with renewed vigor, filling out applications anywhere that would let him, markets, stores, large chain restaurants, small family owned holes in the wall, offering his services to anyone who would give him the time of day. He had been doing this for months, but he could feel that his energy was different this time around. He felt more confident, no longer self-conscious of his shaggy hair and ragged appearance. He now headed out to job hunt freshly showered and in clean clothes. He felt the difference when he introduced himself to a prospective employer, enthusiastically making eye contact and shaking hands without worrying about whether he was omitting an unpleasant stench to which he had become too accustomed to notice. Like body odor. Or desperation. He felt positive and he was convinced that he would get hired soon.

By the end of the week, Dean had been offered a job at a small, family owned convenience store. It was kind of like working at Doose's, but also completely different. The tasks were the same. He stocked shelves, cleaned up and was starting to get trained on the register. The difference was with the customers. The clientele was definitely not what he had seen in Stars Hollow. So far, he had seen frequent shoplifting, often by children that Dean assumed should be in school since he worked the weekday morning shift, a man he was pretty sure was high trying to use his girlfriend's WIC card to buy beer, and, most unbelievably, two young women getting into a physical altercation over the last package of Ding Dongs. And that was just during his first week.

Dean had spent most of his childhood in Chicago, but out in the suburbs. Most of his ventures into the city had been with his parents for family activities like Cubs games or trips to the Field Museum. He had just been getting to the age where he had been allowed to take the L into the city with his friends without adult supervision when they had moved to Connecticut. He had always known deep down he wasn't a city person at heart. He preferred the leafy Chicago suburbs to any part of Chicago other than Wrigley Field, and he now missed Stars Hollow more than anything. He had felt safer there than anywhere else. When he compared Stars Hollow to the city, it made him smile to think that the person who wanted to hurt him the most in Stars Hollow was now the person he felt the safest being around in New York. He was finding this city, or at least the part where he was currently living and working, to be even more unnerving than Chicago. He was grateful that the store had needed someone for the morning shift, because he could only imagine how much seedier the place would be at night. He knew he would have taken the job anyway, regardless of which shift they needed filled. He knew he wasn't in a position to be choosy. But when he imagined the night shift, he pictured himself dealing with drunk customers and being held-up at gunpoint. He was glad that Clara was with their aunt and uncle, who could afford to live in a safer neighborhood just outside the city.

One of the upsides to the job was Angela, the girl who worked the register for most of Dean's shifts. She was only a couple of years older than Dean and was working the day shift at the store and going to community college at night, where she was studying to become a veterinary technician. She was nicer to Dean than most of the people he had encountered in the past couple of months. At first, he attributed that to her personality, that she must be especially friendly and welcoming. It took about half of his first shift for him to remember that this was how normal people treated each other. And, since Angela had never seen him reeking of desperation in dirty clothes that he had slept in for too many nights in a row without washing, she had quickly lumped him into the normal category. He liked the idea that she didn't know about his past and only saw him as a regular person, instead of a victim, of tragedy, or homelessness, or his own stupid decisions. Angela was fun and talking to her while he worked made Dean's shifts pass quicker and gave him confidence that he was still capable of connecting with a new person. Plus, she wasn't afraid to call out the shoplifters, which Dean appreciated, since he hadn't yet worked up the nerve to do that himself and wasn't sure he ever would.

He thought about his life and tried to picture a future for himself as he worked. Realistically, he doubted he would ever be able to live anywhere even remotely resembling Stars Hollow again. Not with minimum wage jobs and no college education. Not that he wasn't grateful for this job, because he was. For sure. It was only part-time right now, but since it was a morning shift he still spent his afternoons looking for a second job to supplement his income. He couldn't wait until the following Friday to get his first paycheck. He was going to cash the whole thing, keep fifty dollars for himself, which he felt was sufficient to get him through the two weeks until his next paycheck, mostly because they were still largely subsisting off the food Luke had bought, and present whatever was leftover to Jess to start paying him back for all he'd done for him. Dean got a warm happy feeling when he thought about that, partly pride at finally being able to start financially contributing and paying his way with Jess, and partly glee at how uncomfortable it will make Jess when he presents him with his heartfelt thanks for taking him in along with the money. He had never met anyone as uncomfortable with being thanked as Jess. Maybe he'd throw in a hug, too, just to make Jess squirm.

Now that he was at least partly employed and feeling better about himself, he knew he needed to find a way to see his sister, even if it meant facing his aunt and uncle. And possibly his cousin. His stomach clenched at the thought, but he knew he couldn't make excuses for himself any longer. It was time.

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"Hey Jess, how was your day?" Dean called from in front of the stove, glancing in Jess' direction with a smile before returning his attention to the frying pan in front of him, the contents of which he was pushing around with a wooden spoon.

Jess looked over to Dean while he started stripping off his gloves and jacket. It still felt weird to Jess that he was as ok as he was with the total lack of solitude and privacy in his apartment. And on some days, like today, he even liked coming home to someone who cared enough to ask about his day. His evenings had been different since Dean had entered his life. He no longer spent the better part of every night escaping his reality, either lost in a book or working on a story on his laptop, but he didn't mind the distraction or the human interaction as much as he had expected to. Dinner now took longer than the five minutes it used to take him to make and wolf down a sandwich and a bowl of soup standing at the counter. Dean, in his eagerness to do something for Jess, had insisted on making dinner almost every night since Luke had stocked their kitchen a couple of weeks ago. He made basic stuff like omelets or pasta, but to Jess, who could remember a time in his life when his own mother couldn't be bothered to cook for him, Dean's efforts were worth the respect of Jess sitting down to dinner and conversation with his roommate. He recognized that Dean needed people around him more than he did, and he knew that the guy was probably lonely, with his parents gone and being separated from his sister, and Jess tried to do what he could to alleviate that. Jess was able to fit in more reading and writing on some nights than others and he had even taken Dean to the library on his day off to get him a library card and some books that appealed to him more than the ones in Jess' collection in hopes that they could spend more time reading in companionable silence. On a couple of evenings when Dean had seemed particularly needy and had interrupted Jess repeatedly while he tried to read, always with a chagrined apology when he realized he had done it again, Jess had abandoned his book altogether and brought out a deck of cards and started teaching Dean to play poker. It's not like Jess didn't have compassion. He did. He just needed more alone time than most people…or at least he had always thought he did. Dean's presence had made him start questioning that deeply held belief and he had concluded that it might not be as true as he once thought if he was around the right people.

Jess pulled his hat off and stuck it on the hook on the wall over his jacket and started working his boots off as he responded. "It was good. Nothing exciting, but nothing to complain about either." This was a new attitude that Jess was trying out. He realized he had spent a lot of time complaining to Luke when he had worked in the diner and he often caught himself taking a mental inventory of his complaints about his job at Kinko's. At first, he felt like he couldn't complain about work in front of Dean, when the guy had so desperately been looking for a job of his own. And now, he was trying to take that attitude one step further and actually be grateful for what he had. Kinko's wasn't exactly a coal mine. He worked in a comfortable, heated store where he wasn't required to do anything dangerous or even that difficult. And he earned enough to feed himself and keep a roof over his head. He wanted to take a page out of Dean's book and feel grateful for that. "Oh, I had my six-month review today." Jess washed his hands at the kitchen sink before grabbing plates and silverware from the cabinet, so he could start setting the table while Dean finished dinner.

Dean grinned at him. "That sounds pretty exciting to me. How did it go?"

"Better than I expected actually. Eduardo said my performance has improved a lot over the last few weeks, especially my attitude. He feels like I've gotten better at dealing with difficult customers without, how did he put it, 'showing them my scowly face.'"

Dean laughed as he strained the pasta over the sink, averting his face as the steam rose up at him. "Scowly face! I love that! It's so perfect for you. Eduardo sounds awesome."

"He's not so bad as far as managers go. He gave me a raise, too."

Dean looked up at Jess. "Congratulations! That's so great, Jess!"

Jess shrugged slightly. "It's only an extra thirty-five cents an hour. It's not like we'll be using it to get a big screen TV or anything anytime soon." Jess heard his own use of the word 'we' and paused, thinking about how quickly he had gone from being someone who needed his independence and solitude above all else to being someone who considered himself part of a team, a 'we', with someone he had previously hated.

Dean had poured the pasta into a bowl and added red sauce from a jar and he was now mixing in the vegetables he had sautéed. "Who cares? Who needs a TV anyway? I don't think I've ever read so much in my life. I kind of wish Rory could see me now." Dean kept his eyes trained on the pasta and kept mixing longer than necessary to avoid Jess' eye, feeling embarrassed for bringing up their mutual ex-girlfriend in that context, as if he still wanted to impress her.

Jess kept silent as he watched Dean curiously for signs of how seriously to take the comment. Dean gave up stirring under Jess' scrutinizing gaze and carried the bowl of pasta to the table while Jess filled two glasses with water.

Dean recovered and began again, his tone light. "It's pretty cool, though, that your manager noticed an improvement in your attitude. It does seem like it's been better lately."

Jess wanted to ask Dean if he still had feelings for Rory, but he recognized Dean's discomfort over his admission and sensed he should let it go without comment. "Oh, really?" Jess raised an eyebrow playfully as he set down the waters and sat across from Dean. "You going to give me a review now, too?"

Dean laughed. "I didn't mean it like that. It's not like I'm judging your attitude or anything. But, I've noticed you seem…happier lately, more positive."

"Oh, yeah?" Jess took a bite of pasta.

"Yeah. I think maybe it was from seeing Luke when he came out here. You just seem…better, I guess. More relaxed."

"Hmm, good to know." Jess nodded, expression serious. "While we're trading compliments, you smell a lot less like shit than you did when you first moved in."

Dean barked out a sharp laugh. "God, Jess, how can you be such a good person and such a complete ass at the same time?"

Jess shrugged, feigning innocence. "It's a gift. I don't question it."

Dean was still shaking his head as he took a bite of pasta. Jess followed suit, chewing his bite slowly and savoring the taste.

"Hey, this is really good, Dean. Thanks for making dinner. Again."

"No problem. I kind of like doing it. I think I'm going to pick up a cookbook the next time I'm at the library so I can learn to make more stuff than just eggs and pasta."

Jess smirked. "Well, aren't you just a regular little Donna Reed?"

Dean snorted, then looked past Jess, lost in thought for a moment before recovering. When he made eye contact again, Jess was watching him thoughtfully.

"So, I think I'm going to go see Clara tomorrow afternoon. I'm still looking for a second job, of course, I know I need one, but I think I need to take a break from looking tomorrow and go out there." Dean took a deep breath. "I think it's time."

Jess nodded slowly. "How are you going to do it? Are you going to call first or just show up?"

"I think I'm just going to show up. I'm going to aim for three o'clock when Clara should be getting home from school, but my uncle should still be at work." Dean didn't mention how this timing had failed him on his attempt to call his aunt and uncle's house. Unless his uncle had quit his job, that had to have been a fluke. Maybe his uncle had been home sick or something. He knew it would go smoother if he only saw his aunt and Clara, and his aunt had gone part-time at her job when they moved in so that she could be home when Clara got home from school in the afternoon.

Jess nodded again. "Are you ok to get there? Do you need any money or anything? I know you don't get your first check until next week."

Dean nodded cautiously. "I should be good. I have enough to get there and back. Not that I have much." Dean rushed to add, feeling uncertain. "Just a little under a hundred dollars in the bank, and thirty-seven on me…I don't want you to think I've been holding out on you or anything. And when I get paid next week, I'm going to start paying you back-"

"Dean, it's fine." Jess cut him off before he started babbling. "I know you aren't holding out on me. You offered me what you had left when you first moved in. I didn't want it. I still don't. It'll be different when you're getting paid again, but I don't want to take anything from you until then. I'm only asking about money now to make sure you have enough for tomorrow."

Dean nodded. "I do. Thanks, Jess."

"And you know how to get there from here?"

"I think so, but I was hoping I could look up the route on your computer tonight to make sure. If that's ok." Jess mostly used his laptop for writing, but he was able to pick up his neighbor's wifi signal so they did have access to the internet. He realized he had never offered Dean the use of his computer before and he probably should have. The internet would have gone a long way toward alleviating Dean's boredom when he had first arrived and been stuck, keyless, in the apartment all day while Jess worked.

"Yeah, of course. You can use my computer for other stuff, too, when you want to. I guess I never really said that, but I'm ok with you using it." Jess made a mental note to go back and password protect all the word documents that held his current and aborted writing projects. He wasn't ready to share that part of his life with anyone.

"Thanks, Jess." Now that he had declared his plan out loud to another person, the idea felt more real and he was starting to feel anxious.

"Dean, I really think it's going to be ok. Unless they're complete assholes, I bet they've been really worried about you and are going to want to make things right." Jess was aiming to reassure Dean, but as he thought about the truth of his words, it hit him that he may not have a roommate by this time tomorrow and he felt himself tensing with anxiety.

Dean forced a small smile onto his face and took another bite of pasta, not entirely convinced that his uncle didn't fall into the 'complete asshole' category.

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"Hey, Jess! How's it going, nephew?" Jess had never really gotten used to how happy Luke always sounded to hear from him. On good days, it made him feel grateful to have Luke in his life, and on not so good days, like the one he was currently having, it made him feel undeserving and guilty for not having appreciated Luke more when he had lived with him.

"Hey, Luke. I'm ok. I'm on my lunch break at work. Is now an ok time to talk?"

"Of course." Luke answered automatically. "Just gimme one sec." Jess listened to him yell to Caesar that he was going upstairs for a minute. Jess had intentionally put off taking his break until two o'clock when he knew the lunch rush would be over at the diner.

"So, what's up, Jess?"

"Nothing much." Jess updated his uncle on his recent performance review and raise, including his manager's comment on his scowly face, knowing that Luke would get a kick out of it.

Luke laughed and congratulated Jess on his raise. "I wish I had thought of that term when you worked for me. It's dead on."

"Yeah, Dean really liked it, too." Jess said, his voice flat.

"Hey, how is Dean doing? Any luck with the job hunt?"

"Yeah, he actually started working at a convenience store this week."

"That's great, Jess! Tell him congratulations for me, too. I'm so happy for him. That must be a real weight off for him, huh?"

"Yeah. It's only part-time, so he's still looking for a second job, but yeah, it's something."

Jess could hear the smile in Luke's voice. "It's definitely something. Good for him!"

"Oh, uh, he wanted me to tell you thank you for the clothes and the haircut and everything. Again. He says he owes getting the job to no longer smelling like garbage and looking like a pathetic street urchin from a Dickens novel."

Luke laughed. "Yeah, that's what he said?"

"I may be paraphrasing slightly. Who can remember?"

"Tell him it was my pleasure. I'm glad I could help. And I'm glad things are looking up for him. How are you doing, Jess? You sound a little down."

"Huh? No, I'm ok."

"You sure, kid?"

Jess sighed, not knowing why it was so hard to bring up what he had called Luke to discuss in the first place. "Dean is going to go see his sister today, at his aunt and uncle's place."

"Oh, yeah? Good for him. He should go see his sister. I'm sure his aunt and uncle have been worried sick about him-" Luke had responded instinctively knowing how he would feel in their shoes but it hit him that he didn't know the story of why Dean had left their home to begin with. "Hey, Jess, do you know what happened there? Did Dean ever tell you why he left his aunt and uncle's house?"

"Yeah." Jess thought for a minute. "You can't tell anyone, Luke. I'm serious. Not even Lorelai. And don't bring it up to Dean. I'm pretty sure he'd be embarrassed for you to know this."

"I won't tell anyone, Jess. I'll protect the secret like it's yours."

"Dean wasn't good when he lived there. He was depressed over his parents and everything, like anyone would be…."

"Jess, I'm not going to judge Dean. I know he's been through a lot. You don't need to tell me if you aren't comfortable with it."

"No, I want to, I just don't want to make it sound worse than it is." Jess took a moment to collect his thoughts. "So, Dean kind of bonded with his cousin's fiancé. They were home from law school for Thanksgiving break and I guess she was really nice to him and sympathetic and listened to him talk about his parents and everything and one thing led to another and they ended up having sex. His cousin walked in on them and beat the shit out of Dean, and his uncle screamed at him and threw him out in the middle of the night. I get the impression his uncle has always been kind of a dick." Jess wanted to defend Dean. "But, I don't think it was about sex. I think it was more about comfort than anything, because Dean was feeling so bad about everything." Jess had a quick flash of himself persistently trying to get past Rory's defenses at Kyle's party. It hadn't been about sex or about her at all, but about comforting and reassuring himself as his life had been sucked into a downward spiral. His stomach clenched with guilt at the memory.

Luke was silent for a moment, processing the story. It hadn't been what he had expected at all. "Ok. It was a dumb thing to do, sure, but people do crazy things when they're grieving. His uncle still shouldn't have kicked out a kid with nowhere to go in the middle of the night. With what it's been like this winter, Dean could have frozen to death if he couldn't find a place to stay." Jess could tell from Luke's voice that he was angry on Dean's behalf.

"Yeah, I know. Throwing him out like that was pretty shitty. I hope everything goes better for him today."

"Me too. I hope they don't give him a hard time about seeing his sister. I hope they realize how wrong that would be."

Jess nodded. Luke was worried about Dean. Of course, he was. Jess knew he should be, too. And he was, but he couldn't shake the idea of how much his own life would change again if Dean moved back in with his family. "Yeah, I hope they're not jerks about it. He's been having a really good week, with starting his new job. I can tell he's been feeling good, and I'd hate to see them upset him now."

"Well, just make sure you're there for him tonight when he gets back, if he wants to talk or anything."

Jess is offended by the implication that he might not be. "Yeah, of course." Jess knew it had come out as a snap, even as he tried to bite back his annoyance that Luke still didn't trust him to be nice to Dean without being prompted like a little kid.

Luke was oblivious to his nephew's tone. "And, even if it doesn't go badly today, there's still going to be a lot for him to process. He's got to be feeling pretty guilty for what he did to his cousin and for going so long without seeing his sister. Just make sure to be there for him, Jess."

Jess snapped. "Yeah, really, Luke, is that what I should do? Wow, sucks that I'm too stupid to be trusted to think of that on my own, doesn't it?" The amount of venom in his voice surprised both of them.

"I'm sorry, Jess. I didn't mean to-"

"No, I'm sorry." Jess sighed. "I'm just in a shitty mood. I shouldn't have taken it out on you like that."

They were both quiet for a moment, then Luke spoke hesitantly. "Uh, Jess. Is this situation with Dean and his uncle upsetting you so much because it makes you think about when I did the same thing to you?"

Jess didn't respond, a little caught off guard by the comparison Luke was drawing.

"You know, when I kicked you out for not graduating high school?"

Jess rolled his eyes, feeling his irritation ebbing away. "Yes, I do know what situation you were referring to, Luke. I was just taking a second to think. And no, I really don't think this is the same thing. I mean, in all fairness, you warned me that I couldn't stay with you if I didn't graduate. And I still didn't put much effort into making that happen. I know that was on me."

"I regret it. I want you to know that. I feel like we should have talked more. Talked calmly, before I told you that you needed to leave."

Jess didn't want to think about this. He was already feeling sorry for himself and he really didn't want to deal with the past, especially with memories from that specific time in his life. It would only make him feel worse. He could still remember sneaking out of Luke's apartment, angry at his uncle, but also terrified that he was giving up his last meaningful connection and the only family he had who had ever really done right by him. He had been scared that he was never going to feel as safe or as cared about again in his life as he had during his time with Luke, but he had still been unable to stay and deal with the mess he had made.

"You don't need to feel bad about it, Luke. Honestly. You gave me the option to stay and go back to school. I was just too stubborn to take it. Plus, you didn't kick me out in the middle of the night. I took off. It's different. I know if I hadn't left, you would have given me time to find somewhere to go. You wouldn't have just put me on the street. And maybe I needed it to happen like it did, in order to get some of my shit figured out on my own. I don't know. But, don't beat yourself up over it, ok? You didn't do anything wrong."

"Thanks, Jess. I just always feel terrible when I think about that time…"

"I know what you mean. I do, too. But, we're good now, right?"

"Yes, nephew, we most certainly are." Jess could hear the smile in Luke's voice. "I'm sorry if I offended you by telling you to be there for Dean. I know you would have anyway. I think I was just talking to try to process the situation, but I shouldn't have said anything like that. I don't think you're stupid and I do trust you, Jess. I hope you know that."

"It's ok, Luke. I shouldn't have snapped at you." Jess smirked. "After everything you've done for me and all the shit you've put up with, I guess you're allowed to say something really stupid every now and then without me jumping down your throat."

"Gee, thanks, Jess. You have quite a way with words. That really warms my heart."

Jess laughed. "You're welcome. I should go clock back in now. My break's almost over."

"Ok, Jess. It was good talking to you. And let me know if there's anything I can do, for Dean or for you. Ok?"

"Ok. Thanks. Oh, hey, Luke, one more thing before you go."

"What is it, Jess?"

"How's Lorelai?"

Luke smiled. "She's good, nephew. Thanks for asking."

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After two subways and one bus ride, Dean stood at the door of his aunt and uncle's house in the cold. He was taking deep breathes and trying to calm himself down enough that he wouldn't look as scared as he felt. It was three-thirty. He wished he had arrived an hour earlier. He could have intercepted Clara on her walk home from the school she attended a couple of blocks away. But, he knew that would have been a cop out. He knew he needed to face his aunt and uncle, or at least his aunt to start with. He knew that having Clara back in his life was going to be worth whatever awkwardness or reprimands he needed to suffer through. Dean took one last deep breath and pushed the doorbell, listening to it chime inside the house.


	9. Chapter 9 - Dean's Family

**Chapter 9 Notes:** Dean visits his sister and things go better and worse than he expected. Thanks to all you are still reading and reviewing this story. I appreciate every bit of feedback I get. :)

 **Disclaimer:** I own nothing except my own obsession with Gilmore Girls.

 **Trigger Warning:** Homelessness. Mentions of death and loss.

It was too late to back out or run away. Dean held his breath as the door was pulled open to reveal his aunt, standing in the doorway with a shocked expression on her face.

"Hi Aunt Gretchen." Dean struggled to tamp down the nerves and keep his voice steady.

Tears formed in his aunt's eyes as she stood there staring at him. Before he could say anything to break the awkward silence, he was being pulled down toward her small frame and hugged tightly. "Oh, Dean, honey. It's so good to see you. I have been so worried about you." She released Dean from the hug, taking a step back, with a hand still on his arm, and leading him across the threshold. "It's freezing out here. Come inside so I can close this door."

Once inside, Dean's eyes swept over the foyer into the living room looking for signs of his sister. Or his uncle or cousin. "Are you ok, sweetie?"

"I am now." Dean could hear the uncertainty in his voice. He wasn't sure if he meant now that Jess had rescued him or now that he was about to see his sister.

"Take your coat off, honey. Come sit down. I'll make us some tea. Are you hungry, Dean?"

"Uh, I'm ok, Aunt Gretchen." Dean started to hesitantly pull off his gloves and unzip his jacket as he followed his aunt into the kitchen, where she was putting on water for tea.

"Clara isn't back from school yet. She has Latin Club after school today."

"Latin Club?" Dean repeated.

Gretchen nodded, pulling out a package of tea bags from the cabinet. "Yes, I don't think she likes it very much, but your Uncle Mel was pretty insistent that she sign up for it this semester. Kevin was in it, too, when he was in junior high school and Mel credits it with his high verbal SAT scores."

"Oh."

"She should be home in about twenty or thirty minutes. She's going to be over the moon to see you, Dean." Gretchen grinned, then, her face lighting up at the idea of Clara being so happy.

"Yeah, I, uh, I can't wait to see her either. It's been really hard being away from her for so long."

Gretchen poured steaming water from the tea kettle into two mugs, added tea bags and brought them over to the table. "Have a seat, Dean."

Dean took another look behind him into the living room as he slowly pulled off his jacket and hung it on a kitchen chair. He realized he hadn't been as subtle as he thought when his aunt read his mind. "No one else is here. Your uncle has been in San Francisco with a client all week. He's flying back today, but I don't expect him home until later tonight. And Kevin is at school."

"Oh, ok. Thanks." He pulled out a chair and sat down opposite his aunt. "Aunt Gretchen, I want you to know that I'm really sorry about what I did. I'm so sorry for what I did to Kevin. I didn't mean for it to happen."

His aunt reached across the table and laid a hand on Dean's forearm. "I know, honey. You were in a bad place. You weren't thinking straight. I know you didn't mean to hurt your cousin like that. You were always a very thoughtful child, Dean. I know that wasn't you."

Dean lowered his gaze to the table, ashamed of his actions. "Does Kevin hate me?" Dean looked up from the table to read his aunt's expression when she didn't respond right away.

"Oh, honey. No, Kevin doesn't hate you. He was just heart broken. He loved that girl. He wanted to marry her. And then to walk in on you two…He was hurt, very hurt, and like his father, he doesn't handle being hurt very well, so it came out as anger. He felt badly, after. For what he did to you. He recognizes that you were dealing with a lot and probably just looking for…comfort. Millicent is a pretty girl. She was kind and she took an interest in you. She should have known better than to do what she did." She patted Dean's arm and then pulled her hand back, cupping her mug of tea.

"It wasn't her fault." Dean instinctively defended Millicent, and regretted it instantly, worrying that it might make the incident look more meaningful to him than it had been, as if he was still pining for her. "I wasn't even interested in her like that. She was just…nice to me." Dean cringed with how pathetic that sounded. Like he was a sad and hurt little boy in such desperate need of affection that he would fall into bed with any girl that was nice to him, even if that girl was engaged to his cousin.

"I know, sweetie. It's ok." She paused to collect her thoughts. "When I think back on everything…I don't think your uncle and I did enough for you. I was so focused on taking care of Clara because she was so young and so sensitive. And you seemed so grown-up and together in comparison, always trying to be there for your sister and helping me out around the house. But, I know you had to have been devastated, too. I don't think we gave you what you needed. I think that played a role in what you did."

Dean wasn't sure what to say so he took a slow sip of his tea. Apple cinnamon. His aunt had remembered it was his favorite. Dean's eyes started to fill at the thought of everything he had given up by his careless actions with Millicent.

"What does Uncle Mel think?"

Gretchen sighed. "You know your uncle, Dean. He's not the easiest man. He's stubborn. It takes him a while to really get over things, especially something he sees as a betrayal." She paused, looking down at her cup of tea. "I'm not really sure what I should say on his behalf, so I'll just speak for myself. You know that your mom and I were friends, right? That I loved your mom before I ever even met your uncle?"

"Yeah." Dean nodded, a small smile forming on his face. "You guys were roommates in college. Mom used to talk about that all the time. How people used to call you guys the odd couple because you were so neat and organized and serious about studying and she, uh, wasn't, I guess."

Gretchen chuckled lightly. "That's right. We were pretty different. But we were best friends. Inseparable all through college and for most of our twenties, even after I married your uncle and she married your dad. Then your uncle and I moved to New York and we didn't see each other as often. But, we were still close. I still love your mother very much." Dean felt his eyes growing damp as he watched tears well up in aunt's eyes, too. She averted her eyes for a moment, then looked back at him before continuing. "Everything happened so fast that night, Dean. I woke up to screaming and fighting. To the shock of what you had done to Kevin. To what Kevin was doing to you. The next thing I knew your uncle was pushing you out the door. I just keep reliving that night. That moment. And thinking about how I let your mother down. How I stood there and watched my husband push her heart-broken baby out the door in the middle of the night." Dean watched a single tear streak down his aunt's face, doing everything he could to hold his own tears back. She reached up a hand and wiped the lone tear away. "Your mother would have been so disappointed in me. I'm so sorry."

Dean shrugged slightly, rubbing at his eyes with the back of his hand. "It's not like I was so innocent that night." He paused to get his emotions under control. "I had just done something pretty terrible to your son. I mean, I get it. You were probably too busy worrying about him to worry about me."

"I should have been able to do both."

Dean heard a key in the lock and before the front door slammed shut, Gretchen had wiped her eyes dry and transformed her expression into one of such genuine happiness that Dean would never have guessed she had been crying if he hadn't just witnessed it. The quickness and completeness of her change in demeanor unsettled Dean, though he couldn't have explained why. "Clara, sweetie, come in here please!"

"Hi Aunt Gretchen, what's-" Clara froze in the doorway to the kitchen, her backpack sliding off her shoulder and landing on the floor with a soft thud. Her face lit up. "Dean!" Dean stood up in time to catch her in a hug as she ran at him, lifting her up and holding her against his chest, her legs wrapping around his waist.

Dean buried his face in his sister's hair, taking in the feel of her weight in his arms. His voice was hoarse with emotion. "It's so good to see you, Clara. I've missed you so much."

"Me too, Dean. I missed you every day! Every minute of every day! I'm so glad you're back." Dean felt a twinge of guilt in his stomach, not sure how back he was. He wasn't sure how welcome he would be once his uncle got home, and he wasn't sure he wanted to hang around to find out. His reunion with his aunt had gone so much better than he had expected. He didn't want to press his luck. He waited for his sister to pull back from the hug first and then set her down on her feet and sat back down in his chair, putting himself closer to her level. Clara pulled a chair right up against Dean's and sat down, pressing her body into Dean's side and leaning her head against his shoulder. He wrapped a long arm around her tiny frame in response. "You're back for good, right? You're staying here again now, aren't you Dean?"

"I'm not sure, Clara-"

"Dean! You have to move back in! I'm your sister!" Clara was starting to cry and it was breaking Dean's heart.

"I know you are. You'll always be my sister…" He thought about what he had done. About facing his uncle and his cousin. And about the time before his thoughtless action. About living under his uncle's roof. Being on guard against the man's irritable moods and caustic temper. The negativity and passive-aggressiveness he aimed at everyone around him. About driving into the city every day with his uncle for the job that Mel had arranged for him in the mailroom of the law firm where he was a partner, the job he hadn't returned to after the night he left out of fear of running into his uncle and being humiliated in public for thinking he would be allowed to keep his job after what he had done. Listening to the man make disparaging comments about Dean's father and not feeling like he could say anything since he was a guest in his uncle's home. Dean didn't want to return to that. But, here was his little sister, crying for him to come back.

"Where have you been staying, Dean?" Gretchen asked.

"I stayed in a motel at first. But, I've been staying with a friend the past few weeks." Dean bypassed the part where he was living on the street and sleeping in homeless shelters to avoid upsetting his sister even more.

Clara looked up, curious. "Which friend?"

"Jess. Do you remember him? You met him at the winter carnival last year."

"Rory's Jess?"

Dean laughed. "That's him. But, he's not Rory's Jess anymore. They broke up."

"I thought you hated that guy. Isn't he the one you got in that fight with right before you graduated? Remember how mad Mom and Dad were at you?"

"I remember." Dean hated remembering the fallout from that fight, how he had deeply disappointed his parents only a few weeks before he had lost them. "And, yeah, that was Jess. We weren't exactly friends in high school, but we grew-up, I guess. We reconnected a while back and I needed a place to stay so he's been letting me stay in his apartment. He's been really great."

"Huh."

"You're welcome to stay here again, Dean." Gretchen said. "To move back in, if that's what you want. But, I don't know if your being here when your uncle gets home tonight is a good idea. I should probably talk to him first, but I'm sure I can work everything out with him. Deep down he's a reasonable man." Gretchen nodded as if in agreement with herself. "Are you able to stay at your friend's place again tonight to give me a chance to talk to your Uncle Mel when he gets home?"

"Yeah, sure." Dean was relieved that his aunt hadn't invited him to move back in immediately. He wanted to be in his sister's life, but he wasn't sure he wanted to commit to moving back into his uncle's house. "I think Jess is good with me staying for a while."

"That's good, honey. He sounds like a really good friend."

"He is. Definitely. Oh, while I'm here, it is ok if I grab some of my stuff from my old room? I could really use my clothes."

Dean felt Clara's head move against him as she immediately looked to Gretchen, and he took in the uncomfortable look on his aunt's face. He felt like he was missing something. He tried to laugh at their reaction, but it came out too nervous sounding to diffuse the tension. "What?"

"It's just." Gretchen started hesitantly. "Well, with what happened the night you left, your uncle was very angry. And then, when we didn't hear from you and it seemed like you weren't coming back…he got rid of your things."

"What?" Dean could feel his temper rising. "That was my stuff! Stuff that I brought with me. From my parents, not stuff he bought me. He had no right to do that, Aunt Gretchen." It hit him then with certainty, he knew he would never move back into this house.

"I know, sweetie. I'm so sorry. I didn't know he was going to do it. You have to believe me. One morning he told me that he was going to work from home, which he didn't do very often, but I didn't really think much of it. And while I was at work, he bagged up all your stuff and brought it to Goodwill. If I'd known he was planning on doing that, I would have talked him out of it, Dean. I'm so sorry."

Dean could feel tears forming in his eyes and blinked them back. He really didn't want to cry in front of his sister. "Is anything left?"

Clara shifted her head to look up at Dean. "I have your framed graduation picture with Mom and Dad. The one you had by your bed. I took it into my room after you left. The photo albums, too. And a couple of your CD's that I was listening to in my room. And you're hoodie, the one from your basketball team. I was wearing it for a while after you left, so it was in my room…but you can have it back if you want it."

Dean cleared his throat and tried to get control of his emotions before he spoke. "That's ok, Clara. You can hold onto it." He couldn't take away something that was giving his sister comfort, not when he knew he wasn't coming back. "At least you had the most important things with you. I hate that I lost all my clothes but losing the pictures." Dean's voice caught, and he paused to get himself under control. "That would have been so much worse."

"I'm really sorry, Dean." Gretchen looked like she was about to cry herself.

"It's ok. It's not your fault." Dean forced a small smile onto his face. He knew it wasn't his aunt's fault, but it didn't make the violation any easier to take. "And Aunt Gretchen, you don't need to talk to Uncle Mel about me moving back here. Because I'm not."

Gretchen lowered her head, looking down at the table. "I understand." She stood up from the table, a small, forced smile on her lips. "How about I give you two some privacy now? I'll be in the living room if you need me."

Clara sniffled and nuzzled her head further into Dean's side like a dog starved for affection. "You aren't going to move back in because of Uncle Mel, right? Because of what he did? He's such a jerk."

Dean nodded. "Yeah, I can't live with someone who threw all my stuff out. I'm sorry. I'm so pissed at him right now, Clara. I can't live under his roof and follow his rules when he could do something like that to me." Dean forced himself to calm down. "Plus, I don't think he wanted me here before I…did what I did. I really don't think he was going to welcome me back now, even if I wanted to come back." The shame of that night flooded back as Dean remembered his sister seeing him the way she had, half naked and getting the snot beaten out of him by their cousin. He really hoped her memory of it wasn't as clear as his was.

Clara wrapped her arms around Dean's waist and squeezed tight. "I get it. I wouldn't want to live here either if I was old enough to live somewhere else." Dean sighed with relief at his sister's maturity, then immediately felt like an asshole for it. A year ago, Clara would have melted down over something like this and screamed until Dean agreed to do what she wanted. A year ago, she still had parents and an older brother who hadn't yet abandoned her and the expectation of being treated with great care by the people she loved most.

"Hey, you like Aunt Gretchen, don't you? You always seem to have a good time with her?"

"I love Aunt Gretchen. She's really nice, and she cares about me. I don't know why she's married to him. Remember how he always said crap about Dad? About him cheating on Mom and stuff and how Mom should have known better than to marry him?" Dean listened to his sister sniffling and knew she was close to tears again.

Dean nodded. "Yeah, I remember."

"Now he says stuff about you, too. Once he called you pathetic and a loser. I told him not to talk about you like that. I said I hated him for throwing you out and that he was the loser. Not you, and not Dad. And he yelled at me. Told me that I was lucky I had him to take me in, but that it wasn't too late to work out other living arrangements if I was going to be so ungrateful after everything he's done for me. He's such a jerk, Dean! I hate him so much! And it's like Aunt Gretchen blocks out the mean stuff he says. She's so nice when he's not around, but it's like she doesn't have a brain when he's here."

"Clara." Dean admonished gently.

"It is!" Clara insisted. "She only thinks about not making him angry when he's home. She doesn't care about anything else. Like this week he was away and me and Aunt Gretchen had so much fun. We played games and went to the mall and the movies and ate dinner in the living room and watched TV. I didn't have to worry about making him mad or him saying stuff that makes me mad."

"I'm so sorry, Clara. I know he's not easy to be around."

"I wish we could go back to Stars Hollow and live together. I don't like it here, Dean. And I'm only twelve. I'm going to be stuck here for six more years." The hopelessness in her voice was breaking Dean's heart.

Dean wished he could go back to Stars Hollow, too. Everything had been easier there, better. He wished his sister could finish school there and spend the rest of her childhood in such a safe, happy place. "I'm sorry, Clara. I wish we could go back to Stars Hollow, too." Dean ran his hand over Clara's hair, trying to soothe his sister.

The girl sniffled quietly. "Why can't I go live with you? You're an adult. Maybe we could rent an apartment in Stars Hollow. Just me and you."

Dean felt a stabbing physical pain at his sister's sadness and he filled with intense shame at his own complete inadequacy. He had a part-time job and was squatting rent free in a friend's house. A few weeks ago, he had been homeless. No one would ever trust him to take care of a child. "Clara. I don't think anyone would give me custody of you. I have a high school education. I'm working a minimum wage job and staying at a friend's place. I don't think I could really impress a judge with my ability to take care of you right now."

Clara sniffled again, burrowing her head deeper into Dean's side. "What about Mom and Dad's money? They must have left you their money, right? Since you're technically an adult?"

Dean sighed. In truth, he was still annoyed with his parents for setting things up the way they had. "Mom and Dad's money is in a trust that's controlled by Uncle Mel. I can't access any of it until I turn twenty-one." Why his parents chose twenty-one instead of eighteen was a mystery to Dean, but he had learned that they hadn't updated their will since right after Clara was born when they had both been on better terms with his uncle and he assumed they had believed that, in the event of their deaths, Uncle Mel would support Dean through college anyway. Plus, he was pretty sure they never really expected their will to come into play before both their children were adults. "But, that's only two more years." Maybe that would change everything. Maybe Dean really would be able to get custody of Clara then. If he worked hard and saved money. Rented an apartment of his own. Established a responsible track record. He didn't want to get his sister's hopes up before he knew what the odds were, but maybe something like that would be possible then. His uncle had threatened her with finding other living arrangements. Fuck that guy. Maybe they would do just that.

Dean looked down at his sister, clinging to him like a drowning person to a life raft. He knew he had to do something. Maybe he could get his shit together without the inheritance money from their parents. People must do this kind of thing all the time when they lost parents. He could work hard. Two, maybe three jobs if he needed to. He would do whatever it took. He couldn't stomach the thought of Clara spending the next six years in a situation where she was so miserable.

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Dean ended up staying at his aunt and uncle's house until late that evening. He wrote down Jess' phone number and address for Clara and found out what her schedule was like and when the best times would be for Dean to call. He went up to Clara's room with her and took a few pictures from one of the photo albums, one of Clara that he had always liked, of her at seven or eight years old, holding a dripping ice cream cone, the expression on her little face serious as she concentrated on it, and another of the two of them smiling and standing knee deep in a lake during a family camping trip a few years ago. One of him and his father after a Little League game back in Chicago, his dad's arm slung around his shoulders, a proud smile on his face, and another of them in the same pose, with grease stained hands, standing next to Rory's completed car. One of his mom kneeling on the floor, a huge smile on her face as she watched a one-year old Dean attempt to walk and another of her tying his tie for him as he had gotten ready to pick up Lindsay for the prom. One Lorelai had taken during a Gilmore movie night, of him and Rory on the couch, his arm around her, Rory smiling at the camera and Dean smiling at Rory. And lastly, out of guilt as much as anything, one of him and Lindsay after his championship hockey game, the look on Lindsay's face echoing his dad's after the Little League game. He wanted some things with him, so he would know they were safe.

Dean and Clara ate dinner with their aunt, and the normalness of the experience surprised Dean. They were in the middle of their third game of gin rummy on Clara's bed when Gretchen came into Clara's room to let Dean know that his uncle had just texted from the cab and was about forty-five minutes away. Dean nodded and thanked her, telling Clara that that was his cue. This would have to be their last hand for now. Clara's face had fallen a little, but she had nodded and focused on her cards. Once the game was over, Dean had hugged her to his side, telling her that he loved her. That he was sorry for how much time he had let pass without seeing her. That he would never do that again. That it didn't matter what their uncle thought of him, Dean would be in Clara's life going forward. He promised. When Clara seemed doubtful and tears ran down her face, Dean had brought her back downstairs and made a plan with his aunt. He would be back on Sunday to meet up with Clara again. He would come to the house to get her and take her out for lunch somewhere and maybe to a movie or whatever she wanted to do. It would be their regular thing. And in the spring, when it was tennis season, he would come to as many of her team matches as he could. He was serious. He promised to be a better brother. He promised that they would never lose contact again.

Dean gave Jess' number to his aunt, too, realizing he would want her to be able to reach him if something happened to Clara. He left Clara and Gretchen in the living room as he went back into the kitchen to collect his coat and hat and gloves, tucking the photos safely into the inside pocket and zipping it shut before shrugging into his jacket. As he walked past his uncle's study on his way back to his sister, Dean's eye landed on the small open-faced liquor cabinet past the desk. Before Dean had time to process what he was doing, he had ducked into the study, shoved a medium sized bottle of something brown inside his bulky winter jacket, and returned to the living room to say goodbye to his sister. As he walked out of house and headed toward the subway station in the dark, he had only one thing on his mind. Fuck you, Uncle Mel.

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Jess closed his book and set it on the floor by his mattress. He checked his alarm clock for the millionth time. Eleven-twenty. Time to face facts and call it a day. Dean wasn't coming back. Jess wasn't as surprised by the outcome as he was by the fact that Dean hadn't even bothered to call to tell him that he was staying with his family. That's what hurt Jess the most. That after all this time and everything Jess had done for him, Dean didn't see Jess as a real friend who deserved a call. Dean was just going to drop him from his life without a word. Whatever. This is why Jess didn't bother with other people. They sucked. He had learned that lesson early in life. Being around Luke and soaking up the Norman Rockwell atmosphere in Stars Hollow had made him forget that truth for a little while, but it was coming back to him now. Luke was an anomaly. Rory had been, too. But that hadn't lasted anyway. Most people were assholes, only out for themselves, ready to use you when they needed something and discard you when they were done with you. He was better off alone. He had always instinctively known that. He had no one to blame but himself for losing sight of that. He got up and switched off the light, ready for this day to be over. The last thing on his mind as his head hit the pillow was a thought that seemed to materialize out of nowhere, that maybe he deserved this for what he had done to Rory, running off to California without saying goodbye. Fucking karma.


	10. Chapter 10 - The Fallout

**Chapter 10 Notes:** The fallout from Dean's visit with his family leads to a very rough night. Thank you to everyone who is reading and reviewing this story. I appreciate all your reviews very much.

 **Disclaimer:** I own nothing except my own obsession with Gilmore Girls.

 **Trigger Warning:** Homelessness. Mentions of death and loss. Drunk behavior that is not good.

Once he made it to the subway platform, still fuming, Dean pulled the bottle out of his jacket to check out his spoils. Macallan 18. Scotch Whisky. Huh. Dean had never had Scotch or Whisky before, his only experience with alcohol being a few beers at high school parties, but he had always thought they were two different things. And shouldn't whisky have an 'e' in it? He hoped this shit was expensive. He hoped his uncle missed it and it pissed him off to find it gone. See how that jerk liked having someone take his shit.

Dean's trip back into the city was a blur. He got a seat at the end of an almost empty subway car and started on the bottle, sipping discreetly at first, gagging and coughing at first, then keeping the bottle to his mouth for longer intervals, drawing in more of the rich, flaming burn as he realized that none of his fellow passengers were bothering to look his way, never mind taking offense at his behavior. Unphased bystanders who had seen it all. That had to be the only good thing about this city. Anonymity when you wanted it.

The more Dean drowned his rage, the easier everything felt. He hated his uncle, but whatever, that was fine. He would just avoid that fucker and never see him again. Problem solved! He wanted to get custody of Clara. He would get another job. Five more jobs. Then an apartment in Stars Hollow. Easy-peasy! He could do it. He was a smart guy. He was responsible. And hard working. And pretty good looking, if he did say so himself. He would work it all out and keep him and Clara together. Kids his age who lost their parents did this every day. He had read The Outsiders. Watched Party of Five. He could get it together like those guys. Sure, he could. What he needed was a lawyer. A super-hot and feisty Ally McBeal of a lawyer. That would be awesome. He couldn't wait to see his dickhead uncle's stupid face when Dean got awarded custody of Clara. Stupid face. His stupid, everything-always-has-to-be-my-way, throwing-out-other-people's- stuff, running-down-other people's-dads, threatening-to-kick-out-other people's-little-sisters face. Dean laughed out loud. Everything felt better. Easier. Dean felt sure now that it would all be ok.

What wasn't easier was transferring to the subway line that would take him to Jess' neighborhood. He had been pretty sure it was fourteen stops in. Or fifteen. But, that might have been a few stops ago when he figured that out. Dean's head was feeling muddy, and he was having more trouble figuring out what to do than he thought he should. He got up on wobbly legs to look at the map of the subway line and almost face planted, catching himself on the shoulder of the guy in front of him. That got him an angry glare and a shove. "Watch it, Asshole." Apparently, the bystanders were only unphased if you kept your distance. Up close, they were ready to attack. Dean tried to apologize, but he could tell it wasn't come out right, and was told to fuck off for his efforts. When he finally made it over to the map, holding on to a metal bar for dear life, he realized he had missed the stop he needed for his connection. He got off at the next stop to board a train going back in the opposite direction. He moved to the far end of the platform, on the other side of a cement column from the waiting crowd and helped himself to more comfort from the bottle. He boarded the next train and collapsed into a seat. He must have nodded off for a few minutes. He woke to find what was left of the Macallan on the floor, pooling in front of him and running in thin brown lines to the front of the subway car. The bottle lay in broken shards at his feet and the seats around him had emptied out. He had missed his stop again. And now, he really needed to piss.

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Jess woke with a start as something connected with the side of his ribs hard enough to hurt. He felt a hand pushing against his chest in the dark, bearing weight, heard soft giggling, smelled the rancid smell of alcohol on breath, felt clumsy fumbling next to him. His heart raced as his mind flew into a familiar panic, automatically trying to remember which one of Liz's boyfriends this was and where he was sleeping so that he could formulate an escape plan, before awareness set in. He was an adult, safe in his own apartment. And apparently, he still had a roommate. "What the fuck, Dean?" Jess grabbed the arm attached to the hand on his chest and pushed roughly. He heard a thud, followed by more giggling, unmistakably Dean's this time. Jess sat up on his mattress, the fear caused by the sudden intrusion of his personal space still evident in the pounding of his heart, but slowly dissipating as his body caught up and realized he wasn't in danger.

"I'm sorry, Jess. Real sorry." His words weren't slurred, but Jess could tell by the way he was carefully enunciating each syllable, as though he was afraid he would forget how to speak if he didn't fully concentrate on the task, that he was drunk. That and the smell. Dean smelled like a drunk. It wasn't a smell Jess was comfortable with. "I tripped and fell on you."

"Yeah, I kind of noticed that."

Dean giggled again. "Sorry 'bout that. I think it was because you were sleeping on the floor, though."

Jess sighed and got up from his mattress, flipped the light switch on the wall, and took in the sight of Dean, still sitting on the floor where he had landed when Jess pushed him, leaning to the side unsteadily, one hand on the floor for support, his jacket, hat and gloves scattered randomly around him on the floor. "Yeah, that's why you tripped? You don't think being drunk off your ass had anything to do with it?"

Dean looked down at himself sitting on the floor. "Actually, Jess, I think I'm drunk 'on' my ass." Dean snorted out a laugh at his own lame joke.

"Jesus Christ, Dean." Jess sighed and glanced at his alarm clock. "It's two o'clock in the morning. Are you just getting in now?"

"Yes, I am. Did you know the subway is very confusing at night, Jess? It's very confusing to people. They should fix that."

"Yeah? I didn't realize the subway got more confusing at night. I did know that it got a hell of a lot more dangerous at night. I don't want to sound like a broken record, but hey, do you think your confusion relates more to the logistics of the New York City subway system or to your current state of decreased mental capacity due to, oh, I don't know, being drunk off your ass?"

Dean shook his head quickly from side to side, before a wave of nausea hit him and he had to stop. "Nope, definitely the logistics of the subway system, Jess. I'm sure of it. Other people looked confused, too."

"Ah, I see. In that case, you should write a letter of complaint to Bloomberg in the morning. You know, this was pretty stupid, Dean. Seriously. Getting this drunk and wandering around the city by yourself. It's dangerous here. You have to be more careful. This isn't Stars Hollow."

Dean looked appropriately chagrined as he listened to Jess. "Sorry." He whispered, eyes on the floor in front of him. "I wasn't wandering. I was trying to get home from my aunt and uncle's. But, it was hard. Today was hard."

Jess softened at Dean's apology, noting how he referred to Jess' apartment as home. Hearing Dean sound like a plaintive child pulled at Jess' heart. Jess' annoyance turned into empathy as he thought about how Dean had spent his day. If he had come back this drunk, the visit with his family couldn't have gone well. Jess sighed and sat down on the edge of his mattress, facing Dean. "Hey, so, how did things go at your aunt and uncle's today? Did you get to see your sister?"

Dean nodded. "Yeah, I got to see her."

"And, she's ok?"

"She's ok. She misses me. I miss her, too."

"What about your aunt and uncle?"

"My aunt was nice. My uncle wasn't there, even. Which was good for me. Clara was happy to see me. I'm gonna start seeing her more. I haven't been a good brother to her, Jess. Not even one little bit."

"It's ok. You'll make it up to her."

Dean nodded emphatically. "I'm going to, Jess. I really am. I'm going to save up money and be responsible and have somewhere to live and get custody of her. So that we can be together. Because that's what she wants. And that's what I want, too."

Jess smiled. "That sounds great, Dean."

"I'll be just like Charlie Salinger. Except, I will still shave my face."

Jess furrowed his brow, searching his brain for literary orphans. "I don't think I know the reference."

"And because my uncle is a dickhead, Jess. Just a complete asshole. She shouldn't have to live with that guy, you know? For six more years. He is the worst."

Jess knew what it was like to live with a man who was 'the worst' and even as he felt sympathy for Dean's sister, he had to force himself to not laugh at Dean's careful and earnest delivery.

"I agree. Living with dickheads is no fun. If there's anything I can do to help, let me know, ok?"

"Ok, Jess. Thank you. But, you're already doing so much for me, Jess. You've been such a great friend to me, Jess. I will never forget how you helped me like this. Ever. I mean it, Jess."

It dawned on Jess how comfortable he had become with Dean. Normally being around drunk men was very triggering for him, but he could admit that, tripping and falling on him while he was trying to sleep aside, he was finding this drunk and serious version of Dean somewhat endearing. "Hey, you don't have to thank me. I like having you here." Jess thought about how true that had become as he remembered how hurt he had felt earlier, when he thought he had been cast out of Dean's life without so much as a phone call to say goodbye. "And, you really don't have to use my name in every sentence." Jess shrugged his shoulders. "Just sayin'."

Dean giggled. "Jess. That's a funny name for a boy. I've only known girl Jess's, and then it was short for Jessica." Dean screwed up his face in concentration. "Is it short for…Jesse?"

"Nope."

"What about… Jestin? Jessrey?"

"I don't think those are even real names. It's not short for anything. It's just Jess."

"Your mom just named you Jess?"

"She sure did. I'm pretty convinced she wanted a girl."

Dean nodded seriously. "My mom wanted a girl, too. After me. And she got one because she had Clara."

Jess nodded, starting to feel tired again.

"I brought some pictures back. You wanna see?"

"Uh, sure. But, then I really need to get back to sleep. I have to work tomorrow. You should get to bed soon, too. It's really late."

"Ok, I will, Jess, I will. I just want to show you these." Dean reached for his jacket laying a few feet away from him and almost fell over. Jess got up to grab it and handed it to Dean. "Thanks." He carefully dug the photos out of the zippered pocket and handed them to Jess, then joined Jess on the mattress, sitting next to him so they could look at the pictures together.

Jess was grateful that there was no drunken commentary to accompany the pictures, but he still gave every photo a moment of his full attention before moving on to the next, not wanting to be disrespectful to something that meant so much to Dean. He startled when he got to the one of Dean on the couch with Rory, transfixed by Rory's image, and concerned about what this meant. He hadn't realized how long he had been staring at it until Dean spoke up quietly. "There's one more." Jess moved the photo of Rory to the back of the stack and was relieved to see the next one included Lindsay instead. Most days, except those when he was feeling especially vulnerable, Jess believed he was completely over Rory, but it still made him happy to see that Lindsay looked much more into Dean in the last picture than Rory did in hers.

"Those are great pictures, Dean." Jess handed him back the stack. "Thanks for letting me look at them."

"Thanks, Jess. They are great." Dean swayed to one side a little as he sat on the mattress.

"Hey, maybe you should get ready for bed. Sleep off whatever you drank. I'll get you a glass of water and dig out the aspirin. You should probably take one before you go to sleep." Jess got to his feet and headed the few steps to the kitchen. "I'm glad you're back, Dean. Even if you are a drunken mess. When I didn't hear from you, I started to think you weren't coming back."

Jess turned back from the sink, a glass of water in one hand to find Dean staring at him silently, his expression a mixture of suspicion and such intense anger that it halted Jess in his tracks, giving him an uneasy feeling in his gut. "What?"

Dean was slowly and gracelessly getting to his feet, the pictures falling to the floor, forgotten. Jess instinctively took a step back.

"You didn't think I was coming back? What do you mean, Jess? Huh?"

"I, uh, I thought you might end up staying at your aunt and uncle's. That's all I meant. What's with you?" Jess could feel his heart rate picking up for the second time that night. This was how he remembered drunk men. The anger. The intimidation. The emotions that changed dramatically, without warning, as if a secret switch had been flipped.

"So, what did you do, Jess? What did you do since you thought I wasn't coming back?"

"What are you talking about? I didn't do anything."

Dean took two steps towards Jess. "Did you throw out my stuff? What the fuck? You had no right to do that, Jess! That was my stuff!"

"What? I didn't throw out anything. I don't know what you're talking about." Jess did his best to keep his voice calm and even, trying to diffuse the situation by not engaging.

"That's a pretty messed up thing to do to somebody, Jess!" Dean's voice was getting louder and louder. "God, I was right about you in high school! You are such as asshole! I should have just stayed on the street!"

"Dean, calm down." Jess kept as much distance as he could between them in the small apartment as he tried to placate Dean. "I didn't throw out any of your stuff. It's all still here. I promise."

Dean took an angry half step forward before pivoting and launching himself onto his knees on the floor in front of the plastic chest of drawers that held his clothes. "My stuff better still be here! You're such a lying piece of shit! I can't believe you did this! You shouldn't throw out other people's stuff, Jess!" Dean started tearing through the container pulling out shirts, socks, underwear, throwing everything haphazardly onto the floor around him. "You're such a jerk! You don't care about anyone but yourself! You think you're so much better than everyone else! But, you're not! You're such an asshole! You had no right to do this!"

Jess watched the toe of Dean's shoe scuff across the picture of his dad at the baseball field, sending it skimming across the floor, stopping a couple of feet behind Dean. Jess set the glass of water on the counter, crouched down and started gathering up the photos, knowing Dean would regret it later if he damaged them during his drunken rampage.

Jess was just picking up the last picture and standing up when Dean turned from the now empty storage container and noticed what he was doing. "What the hell are you doing with those, Jess? Were you trying to throw them out, too?"

"No, Dean, of course not!" Jess was starting to get angry back at Dean, having had his fill of being wrongly accused. "I didn't want them to get ruined while you were throwing a fit, over nothing! All your shit is still here! Did you not notice that while you were trashing the place?"

Dean continued as if Jess hadn't spoken at all. "Those are all I have left of my parents, you asshole! I can't believe you were going to throw them out behind my back!"

"I wasn't! Here, take them!" Jess held out the stack of photos.

Dean knocked his arm into Jess' hand. Hard. The pictures went flying, landing scattered on the floor. "You think you're so much better than me, don't you, Jess?"

"No, I don't, Dean. Of course, I don't." Dean was up in Jess' face now, looming over him, Jess backed against the counter. Jess averted his eyes, not wanting to make eye contact and escalate the confrontation, and his gaze landed on the picture of Dean's mom, alive and happy and hopeful for her son as she helped him tie his tie. Jess' heart clenched at what Dean had lost.

"You've always thought you were better than me. You thought you were smarter than me in high school, just because you read so many books. But, I think that just meant you had no friends. Then. Now. I've been living with you for almost two months now and you've never gone out with anyone. Never even once. Not a friend. Not a girl. And then you stole Rory from me. You thought you were so great, then, didn't you, Jess? So proud of yourself? Rubbing it in my face all the time. Did you know that Rory and I stayed friends? That we kept hanging out even while you were dating? That one time she asked me if I gave you a black eye? She said you had told her I didn't do it, but she didn't believe you, did she? She never really trusted you. Never really loved you. Not like she loved me. Trusted me. I just want you to know that."

Jess could feel Dean's breath on his face, rotten with alcohol. "Ok, Dean. Knock it off. You're just drunk. Let's just go to bed."

"Fuck you, Jess! You think you can tell me what to do? Go to hell! You think you're so great because you have an apartment and I'm homeless? Your parents bail on you and someone like Luke jumps in and wants to take care of you and be your dad." Dean took a step back and dipped his head to the side clumsily, trying to force Jess into eye contact. "I lose my parents and my asshole uncle kicks me out on the street in the middle of the night. You think that's fair? Huh?"

Jess snapped, craning himself up into Dean's personal space, looking him in the eye, voice dripping with sarcastic anger. "You know what, Dean? I didn't think it was fair at first. Not at all! I thought it sucked! But I'm starting to see it from your uncle's side now. Cause this right here." Jess moved one hand back and forth between him and Dean. "This makes you a pretty shitty houseguest in my book. And, that doesn't even take into account you sticking your dick where it didn't belong-"

Jess was embarrassed later, when he thought about how caught off guard he had been and how easily he had gone down. He felt Dean's fist connect with his face, just under his left eye, felt his lower back slammed hard into the edge of the counter, felt the floor colliding with his hip, his shoulder, his head as he landed in a heap on his side. He lay there with his arms folded instinctively over his stomach, bracing for what always came next, the kick while he was down. Rory's likeness smiled at him from the floor in front of his face. He felt like he was going to cry. He had made it through the long, drawn out fight at Kyle's party and countless physical altercations with Liz's boyfriends and husbands without crying. This felt different. He felt hurt and betrayed. And hopeless. Emotionally wiped out. Everything seemed to end up the same, no matter what he did.

Then Dean was crouched in front of him, his expression one of shocked disbelief. "Oh, God, Jess. I'm so sorry. I am so sorry." Dean looked as upset and freaked out as Jess felt. "I'm sorry. I can't believe I just did that."

Jess sat up warily and Dean nervously scrambled back a couple of feet to give him space, not sure what to expect in terms of retribution.

A tear streaked down Dean's face, but Jess had been able to hold his back, letting his emotions shift into anger. He regarded Dean's tear coldly, assuming he was just worried about getting thrown out on his ass in the middle of the night. Again. For hurting someone who cared about him. Again.

"Jess? Are you ok?" Dean's voice was thick now, with drunken emotion.

Jess stood up slowly and walked purposely past Dean to his mattress. He was fuming. He could feel his body vibrating with anger. He really wanted to be alone right now. And if he couldn't have that, he needed to go to sleep. He desperately needed this night to be over. He considered turning off the light but figured he would only be inviting Dean to trip over him again on his way to the bathroom. He lay down without a word, his back to Dean. He was done. He couldn't deal with anything else tonight. Not without completely losing his shit.

"Jess? Jess, are you ok? I am so sorry." Jess just ignored him. "Jess? Please say something. I'm so sorry." Jess tried to block out Dean's voice and his quiet crying. "I'm so sorry. I didn't mean to. Please believe me." Then very quietly. "Do you want to hit me back? You can if you want."

After a few more minutes of sniffling, Jess heard Dean on his feet, moving clumsily around the room. "I'll just go, Jess. I'm really sorry. Thanks for everything you did for me. Really. I'm sorry I ruined everything." Dean's voice caught on the last word.

Jess turned then to see Dean, bundled into his jacket and hat, heading toward the door, the one sweatshirt he had brought with him clutched in his hand, all the clothes Luke had bought him still strewn around the room. Jess knew it wouldn't be right to let Dean walk out the door still drunk, at this time of night, in this kind of weather. But, part of him wanted to let Dean go. Fuck that guy. Fuck all the buried hatred he'd been harboring toward Jess. Fuck him for being a disappointingly typical angry and violent drunk. Let him see how far he could get on his own, without Jess' help. Let him end up back at St. Sebastian's for all Jess cared. Dean slipped on a sock and stumbled a little as he made his way to the door. Jess sighed and got out of bed, reaching the door just as Dean was pulling it open. Jess reached past him and pushed the door as hard as he could, needing a physical outlet for his frustration that wasn't Dean's face. The door slammed shut in front of Dean with a loud bang. "Don't be stupid, Dean. Go the fuck to bed."

Dean turned and stared at Jess in surprise, looking young and scared, tears drying in tracks on his face, new ones pooled in his eyes.

Jess sighed again. "C'mon, Dean. Just go to bed. We'll work everything out in the morning." Jess knew what he had always wanted to hear confirmed after he had pissed Luke off when he was staying with him in Stars Hollow. "Tonight sucked, but you still live here, ok? Let's just go to bed."

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Jess didn't usually mind working Saturdays. He had Sunday off every week, unless he needed to cover for someone who was out sick, and his other day off varied, but was always a weekday. He didn't have much of a social life. Dean had been right about that. So, he was not usually any more tired on Saturdays than he was any other day of the week. Not like some of the guys at work, who showed up late, or were tired and hungover when they were forced to work weekend shifts. Not Jess. Except for today. He was bone tired this morning. Completely exhausted. From lack of sleep, and from all the emotional and physical damage from the night before. He had rolled in almost twenty minutes late, half asleep, with a very noticeable black eye. Eduardo had frowned in disapproval at Jess' eye, and Jess had cringed with embarrassment and muttered a quick apology under his breath before ducking into the break room to punch the time clock.

It didn't seem fair to Jess that he was suffering all the effects of having had a wild Friday night without having gotten to experience any of the fun parts of a night out. He could only hope that Dean would feel worse when he finally woke up. It would serve him right. Jess had left him the bottle of aspirin, a glass of water and the bathroom trash can on the floor in easy reach. That was all he could do. He had debated waking Dean and making sure he was ok before he headed out, but Jess hadn't felt like he was ready to deal with him yet. Not when he was still so hurt from the night before. Better to take the day and think things over and talk to Dean later.

Around eleven o'clock, Jess felt his phone vibrate in his pocket while he was working on a printing job. He had a text from Luke: 'Can you please call me today when you get a chance?'

Then another one: 'It's nothing bad'.

Jess was curious, but just responded that he would take his lunch break around two and call then. It was unusual for Luke to text him to call, but Luke wasn't a liar, so he took him at his word that it wasn't something bad and didn't stress over it.

He made the call from the hallway leading to the loading dock, where he would have privacy at this time of day.

"Hey, Jess! Thanks for calling."

Jess could hear the smile for him in Luke's voice and it made him feel a little lighter, like everything was ok. "Yeah, of course. So, what's up? You've built up all this suspense and got me all curious."

Luke laughed. "It's nothing big, really. Just something I wanted to ask you. An idea I wanted to run past you, I guess. No pressure. Just wanted to see what you think about something."

Jess tensed. It wasn't like Luke to hem and haw like this unless he was about to say something that he knew wouldn't go over well with Jess. "Ok. What is it, Luke?"

"Well, just know that you don't have to say yes, but if you-"

"Just ask me, Luke." Jess still felt anxiety from last night and he couldn't take being jerked around right now. "Sorry, I mean, whatever is it, just ask me. Ok?"

"Ok, sorry, nephew. I guess I'm a little nervous, here." Luke laughed self-consciously, and Jess' apprehension mounted as he waited for Lorelai's name to come up. "Anyway, so, Lorelai's parents had these tickets to, uh, the matinee performance of that show The Producers on Sunday, but Emily, uh, Mrs. Gilmore isn't feeling well, and so they can't go. And, uh, Mrs. Gilmore gave the tickets to Lorelai and she invited me since we're together now and everything, so we'll be in New York tomorrow. The show is at three, and I know it's last minute, but since it's usually your day off and everything, we wanted to see if you and Dean wanted to meet up with us for lunch. You know, nothing fancy. Just a casual lunch somewhere to catch up. My treat. Lorelai really wants to see Dean, and you, too, of course. And, you know I always want to see you. And I thought it would be nice for us to all be together. We both thought it would be nice. So, uh, what do you think, nephew?"

Jess sighed. The second to last thing he wanted to do was spend any part of his day off in the company of Lorelai Gilmore. The absolute last thing he wanted to do was hurt his uncle's feelings when the man had so earnestly and nervously just asked him to make an effort to spend time with his girlfriend. And he knew that saying no would do just that. He didn't have a gauge on Lorelai's interest in Luke, but he knew Luke had been in love with Lorelai for years and that if Luke had his way, this would last, possibly ending in marriage someday. He knew he needed to put in the effort with his uncle's girlfriend, no matter what he thought of Lorelai as a person. Luke deserved that from him, at the very least. And, he liked seeing Luke happy and making the man feel like he hadn't wasted his time on Jess.

Jess thought about how he had been so good at saying no to Luke in the past, when the man had told him what to do or yelled at him about something. When Luke had told him to go to school, or what time to be home by, or how to treat girls he dated. He had been fine then with basically telling Luke to shove it and doing whatever he wanted to do. This was harder. Now that Luke treated him like an adult that could be trusted to make good decisions and be there for the people he cared about. Even though he was given the choice now, maybe even because of it, Jess found it so much harder to not do what Luke asked of him. Not that he asked much, anyway.

"Ok."

"Yeah? Really?" Jess could hear the happy relief in Luke's voice, and it made him feel a little like a jerk to know that Luke had had doubts about whether Jess would be cooperative.

"Yeah, I mean, I can't speak for Dean, but I'll ask him tonight and text you."

"Ok. Great. That's great, Jess."

"And, if for some reason, Dean can't make it, I can just let you two have a date and see you another time. If you want."

"Why would I want that, Jess?" Jess heard the disappointed frown. "I hope Dean can come, too, but either way, I'd still love for you to join us. I haven't been to New York since you moved there without seeing you. You're the biggest draw that city has for me, kid." Jess could tell Luke was smiling again. "Without getting to see you, it's just a trip into a dirty, crowded city to watch some show about Hitler putting on a musical."

Jess laughed. "I'm pretty sure that's not an accurate synopsis of The Producers."

"Lorelai gave me the flyer to look at, but I admit I only skimmed the description. I want to be happily surprised when it surpasses my expectations. Plus, she had me at Broadway."

"Oh, yeah? I had no idea you were such an aficionado of the performing arts."

Luke laughed. "In addition to my love of the performing arts, Broadway is appealing to me because of its proximity to my favorite nephew. I was sold at the idea of getting my favorite boy and my favorite girl together. I would even sit through that show about the Irish tap dancers if I had to. That's how much it means to me. I really want you guys to get to know each other better, Jess."

Jess sighed. "I know you do. I can't speak for Lorelai, but I'll be there on Sunday, with or without Dean, with an open mind and a big smile, ready to make a new friend."

"I know you're probably being sarcastic, but I'm going to pretend you're not."

Jess laughed. "Hey, whatever gets you through."

"Thanks, Jess. This really means a lot to me."

"Jeez, Luke, if you start getting emotional on me every time I meet you guys for lunch, I promise that me and Lorelai are going to have one very short-lived friendship."

"Ok. Ok. No emotions here, I swear! I'll text you the name and address of the restaurant. Lorelai is going to pick a place, probably somewhere near the theater."

"That would make the most sense."

"Hey, one more thing. How did it go for Dean with his aunt and uncle yesterday? Did he get to see his sister?"

"Uh, yeah. He got to see her. I don't know any details. He got home pretty late and, uh…we went to bed. I'm sure I'll hear more about it tonight. Maybe he can tell you about it himself at lunch tomorrow."

"Ok. Tell him I say hi and that me and Lorelai are looking forward to seeing him tomorrow."

"Will do."

"All right, kid. I love you and I'm looking forward to seeing you tomorrow, too."

"Me too. Love you, too."

Jess got off the call feeling good about how happy he had made Luke. And making his uncle happy was the only good reason Jess could think of for him to ever subject himself to Lorelai's company, even for just an hour or so over lunch. He stopped in the restroom on his way back to the break room to wash his hands before he ate lunch. He almost jumped at his reflection in the mirror. Shit. The ache had dulled to the point that the bruise had nearly slipped his mind. Now he would have to explain his black eye to Luke. With Lorelai sitting right there judging him. Jess had a bad feeling about this lunch. His own personal hell, Gilmore Friday night dinner revisited.


	11. Chapter 11 - Jess & Dean Work Things Out

**Chapter 11 Notes:** Jess and Dean make up, but it takes them so long to do it that lunch with Luke and Lorelai won't be until the next chapter. I want to really focus on the lunch scene on its own and don't want to tack it on to this chapter. Thank you to everyone who is reading and reviewing this story. Your reviews are much appreciated and have kept me feeling warm and cozy all winter. :)

 **Disclaimer:** I own nothing except my own obsession with Gilmore Girls.

 **Trigger Warning:** Homelessness. Mentions of death and loss. Drunk behavior that is not good. Mentions of prior abuse.

Jess spent the remainder of his shift pondering his two most pressing concerns, how to handle his upcoming lunch with Luke and Lorelai and what to do about his current situation with Dean. He hadn't come up with a solid strategy on how to approach either situation by the time he clocked out. He walked home slowly, enjoying the luxury of the weather allowing him to slow his pace a little. It was late February and still winter weather to be sure, but much improved from the low single digit temperatures that had plagued January and early February, when it had felt impossible to do anything other than keep your head down and walk as fast as you could to your destination when outdoors.

He stopped in at the small market near his apartment. He picked up a basket and wandered the aisles, picking up some eggs, a carton of orange juice, some milk and a box of cereal, he paused at the yogurt as his hand instinctively went toward the pineapple flavor. Dean's favorite. Jess couldn't stand it. He sighed. He knew he needed to get his head straight about what was going on with him and Dean. Either he could forgive Dean for what he had said and done and they could remain friends, or he couldn't, and they couldn't. But, either way, he didn't want to be the kind of person who acted as if everything was ok on the surface and then passive aggressively punished him when he got the chance, by doing petty little things like denying him pineapple yogurt. He was embarrassed at his instinct. It felt like such a 'Liz' thing to do. He remembered so many instances from his childhood when Liz had 'forgotten' to buy him something he needed for school, or take him somewhere, or sometimes even pack him a lunch or make him dinner because he had caused trouble or pissed off one of her boyfriends in some way the night before. He didn't want to be like that.

He knew he needed to make up his mind and make a decision. He was pretty sure he didn't want to end his friendship with Dean or ask Dean to leave, but he still just felt so hurt when he thought about the night before. So, painfully and vulnerably hurt, remembering Dean up in his face, telling him he had no friends, that Rory never loved him the way she had loved Dean. It had all been so familiar and so triggering. Someone running him down for his anti-social tendencies and digging into his personal insecurities, and then hitting him to shut him up when he had verbally fought back or defended himself. He had lived through the same experience so many times in his life, in so many apartments, with so many drunk and angry men. But, it had been a long time since the experience had caught him by surprise and reduced him to the level of hopelessness and self-pity that he had felt the night before.

It was hard for him to logically process wanting to stay friends with someone who had made him feel so terrible. He normally prided himself on his self-preservation instinct, and his total unwillingness to put up with other people's shit. In the past, he had ended friendships for far less serious slights. Jess made up his mind. He put four containers of pineapple yogurt into his basket for Dean along with four mixed-berry for himself. He realized that the shopping could have waited until morning, and he knew that he was just putting off going home. It was time to face Dean. They needed to talk. As bad as today had been for him, dwelling on the events of last night, he knew it had probably been just as bad for Dean, if not worse, since Dean had more guilt to fixate on. On his way to checkout, Jess grabbed a package of saltines and a refrigerated bottle of purple Gatorade. Just in case Dean was still feeling like shit from last night and needed something that wouldn't upset his stomach. Jess smiled to himself, feeling good about his decision.

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Jess walked into the apartment to find Dean asleep in bed, the light was on, the glass of water was empty and there was a book lying next to the head of the roll up mattress that hadn't been there last night. Jess quietly set the bag of groceries on the counter and hung up his jacket and hat, pulled off his gloves and shoes. He washed his hands at the sink, not turning the faucet on full blast so that the sound wouldn't wake Dean, and he started putting the groceries away. Jess was still tired from the night before, too, and it was very tempting to skip dinner and just wash up and go to bed, avoid any conversation altogether. But, he knew he would just be delaying the inevitable and he really didn't want the tension from the previous night hanging over them for another day, especially not if they were going to meet up with Luke and Lorelai tomorrow.

Jess finished putting everything away and walked over to Dean, crouching down next to him, the bottle of Gatorade in his hand. "Dean. Hey, Dean." This time Jess kept his hands to himself remembering how Dean had swung out at him in panic the last time he had woken him up. When he got no response, Jess' voice got firmer, and a little louder. "Dean!"

Dean stirred and groaned softly. His face looked pinched in discomfort as he woke up, and for a second Jess felt guilty. Maybe he should have left this until tomorrow and let Dean sleep the day away in peace. "Hey, Jess…" Dean's voice was hoarse, and Jess recognized the moment when Dean registered the bruise on his face and the events of the previous night came flooding back to him. Dean's expression faltered, and his words trailed off uncertainly. Jess saw shame and guilt in his eyes, and his first rogue thought, before he quickly reigned it in, was good, serves the fucker right, Dean should feel like shit about what he did.

"How are you feeling?"

Now, fully conscious, Dean looked at Jess warily, expecting the worst, knowing he deserved it, and thrown by Jess' calm and concern. "Pretty bad." Dean answered slowly. "I've definitely had better days." Dean pulled himself up to a sitting position and a wave of nausea hit him at the movement. He took a couple of slow, deep breaths. He had spent the better part of the day vomiting and wasn't eager to go another round kneeling at the toilet, especially with Jess home to witness it.

Jess say down on the edge of his mattress. "I know what you mean. My day sucked, too."

Dean put one hand to his head, rubbing his temple, trying to massage the pain from his head.

"I brought you this." Jess held out the Gatorade. "It should help if you're still dehydrated and have a headache. I got you some Saltines, too. I figured they would be easy on your stomach if you were having trouble holding stuff down. They're in the kitchen."

Dean took the Gatorade. "Thanks, Jess. I really appreciate that." He screwed off the cap and took a small sip, testing out its effect on his stomach.

"No problem. It's the stuff Liz always liked after she'd gone on a bender. And I figure she was a pro at hangovers, so…" Jess shrugged, not really sure why he had brought up his mother or where he intended this train of thought to go when he had started speaking.

Dean's stomach clenched at the comparison to Jess' mother while he was taking another sip of Gatorade and for a moment he thought it was going to come back up. "Jess. I'm so sorry about last night. For everything. For hitting you and for everything I said to you, and for coming back to your apartment drunk like that to begin with. I'm so sorry." Dean paused, looking down. "I feel like an asshole for doing what I did, especially after everything you've done for me." Dean could feel himself tearing up. His head was still throbbing. He felt nauseas, his body ached like he had the flu, and, he was somehow still exhausted, even after sleeping most of the day. And he had no self-control left to hold his emotions in.

Jess nodded slowly. "Thanks, Dean. I, uh, I can't tell you it's ok. Because it's not. But, I can honestly tell you that I forgive you."

Dean looked up at Jess. "Yeah?"

Jess gave Dean a small smile. "Yeah. I think I do. And, I get it. I said some shitty things last night, too. I'm not proud of myself, either. And, I'm sorry, too."

"No, Jess." Dean shook his head carefully, trying not to make himself dizzy. "You don't owe me an apology. I was being a complete asshole. You only said stuff to me when I wouldn't stop. I was terrible. And then I… hit you. And I am so sorry for that. I just, I regret that so much. I'm so sorry. And you hadn't even done anything. You have been so good to me. Putting a roof over my head like this. Feeding me. Being there for me when I had absolutely no one." Dean sniffled. "You've been so much better to me than I deserved. And I was mad at my uncle and I took it out on you. The person who's helped me the most. And I'm so sorry."

"What happened with your uncle? Did he throw out your stuff?" Jess huffed out a soft laugh at Dean's look of surprised confusion. "I'm not reading your mind or anything. Last night, you kept accusing me of throwing out your stuff while you were gone. You were really pissed about it, too." Jess shrugged slightly. "So, I just kind of wondered…..."

"Yeah, he donated everything I owned to Goodwill after I left."

"Like everything, everything?" Jess has a flash of memory of a stepfather he had had when he was nine, who had thrown his small collection of books into the dumpster in the alley behind their apartment as punishment for Jess telling him to go to hell and leave him alone.

Dean nodded. "Yeah, everything. My clothes. My CD's. My books. My personal stuff. The room I stayed in looked like I'd never been there."

"That sucks. I'm so sorry, Dean."

"Clara had our family photo albums in her room when he did it, so at least that stuff was safe. The worst was that I had some letters and cards and stuff that I kept in the box with my CD's, and they weren't there anymore, so I'm guessing that stuff got tossed, or maybe sent to Goodwill with the CD's if he didn't notice it. There were some cards from my parents. Letters from Rory when she spent that summer in D.C., a few from friends in Chicago. Some clippings from the Gazette from whenever I got mentioned for basketball or hockey…Stuff like that."

"Your uncle sounds like a complete dick. I can understand why you wanted to drink yourself into oblivion last night." "And why you were so angry."

"I shouldn't have taken it out on you. You had nothing to do with any of it. I'm so sorry."

"Ok. It can't happen again, though."

"It won't, I swear, Jess! I will never do anything like that to you again. I'm so sorry."

Jess looked uncomfortable and averted his eyes, and Dean started to feel nervous. Maybe Jess forgave him but didn't necessarily want him in his apartment any more. "I mean." Jess continued. "The drinking, too. I just, uh, I don't want to tell you what to do, or anything, but I've had a lot of bad experiences with people drinking around me and basically taking shit out on me because of it, and I'm not really comfortable around it."

"Oh." Dean hadn't expected that.

"I don't mean I'm completely straight edge or anything. I've had a few beers in my life, and when I lived with Luke, he would have a beer after work some nights and I was always fine with that, after the first couple of times at least." Jess could remember keeping a furtive eye on his uncle the first time he had ever seen him grab a beer to unwind after work, worried that Luke would turn out to be like so many other men that Jess had lived with before him.

"I get it. You trusted him."

Jess nodded. "I trusted him because he always stopped at one. Maybe two if the Red Sox had a particularly tough loss that night." Jess gave Dean a small smile. "I don't trust anyone when they're drunk."

"I understand. I'm really sorry and I promise I will never come back here drunk again, Jess. I get why you're not ok with it. And, nobody would be after the way I acted last night."

"Thanks. And, could you maybe not come back here buzzed either? I mean, I know that's a lot to ask. We're nineteen and I get if you want to drink, and-"

Dean cut Jess off. "Yes, that's no problem. Of course, Jess. I'm so grateful that you've let me stay here. I'm so grateful that you're not kicking me out after last night. You're not, right?"

Jess smiled. "I'm not kicking you out."

Dean smiled. "Ok, just checking. I promise I won't drink at all while I stay here, Jess. I'm not much of a drinker anyway. I always thought people who got drunk at high school parties were ridiculous. And, now, I don't have the money for it and I wouldn't even know where to get alcohol if I wanted it. I swear, no more drinking. At all. I promise."

"Thanks. I appreciate it." Jess reflected on what Dean just said. "Where did you get the alcohol last night? You just said you didn't have the money for it and wouldn't know where to get it? Were you with that girl you told me about from work?"

"Oh, uh, no." Embarrassment colored Dean's face. "I, um, swiped it from my uncle's study."

Jess laughed. "Seriously? A little payback for tossing your stuff, huh? I like it."

"Sort of. I mean, I didn't plan to take it. I was just walking past his study and saw the bottle and grabbed it and stuck it in my coat before I even thought about it. You know when you do something wrong without really thinking it through, it just seems like a good idea in the moment?"

Jess laughed again. "Oh, I know. Trust me, I know. But, where did you go to drink it?"

"Uh, I didn't really go anywhere…."

"You didn't stand around outside drinking it, did you? It was freezing last night."

"I guess I kind of drank it on the subway."

"Holy shit, Dean! You're lucky you didn't get arrested. You know that, right?"

Dean nodded. "Yeah, it was pretty dumb."

"It was very dumb! You can't drink in the subway. The transit cops are serious about that shit Dean. And they're pretty much all dicks, probably because they're stuck being transit cops. You could have ended up spending the night in jail. And as drunk as you were, I bet you wouldn't even have remembered my phone number to call me for bail. You were really lucky, Dean."

"I know. I kept falling asleep on the train, too, and missing my stop, and at one point I had to pee so bad that I, uh, peed on the tracks while I was waiting for the next train. It's so embarrassing to think about now."

"Wow, no fear of the old peeing on the third rail urban legend, huh?"

"Uh, not last night, I guess. I didn't get electrocuted though. So, that's something."

"I'm actually a little impressed. I don't think I could ever do that. Then again I've never been as drunk off my ass as you were last night." Jess started to laugh, then stopped as he pictured a drunk Dean standing on the subway platform, close enough to the edge that he could urinate over the side onto the tracks below. He wouldn't have been the first drunk to fall onto the tracks and die from electrocution or impact with the train. The idea scared Jess, but he felt like he had already lectured Dean enough about drinking. "Jeez, Dean. You had quite the evening."

"Yeah, full of reasons to never drink again."

Jess was staring past Dean in thought when he remembered to bring up lunch with Luke and Lorelai. He turned back to Dean. "Hey, Luke and Lorelai are going to be here tomorrow. They're going to see 'The Producers' on Broadway. I guess Lorelai's mom gave them free last-minute tickets and they want us to meet up with them for lunch before they go to the show. Are you in?"

Dean frowned. "I would like to see them, definitely, but I can't tomorrow. I have plans with Clara. We're going to make Sunday our day to go out for lunch and do something together. I can't cancel on her the very first Sunday."

"So, Bring her. You just said you were going to take her lunch anyway. Come with us. Luke buys us lunch, then you and Clara do something in the city after, just you two. We have tons of museums and things to do, you know?"

"I know, but I can't just show up with my sister if Luke just invited you and me. It would be rude."

"Luke won't mind. I'll text him right now." Jess stood up and walked over to the coat hooks, pulling his phone out of his jacket pocket and typing quickly. "See?"

"Oh, shit, Jess!" Dean stood up, too, realization hitting him. "I can't see Luke tomorrow, are you crazy?"

"What's the matter?" Jess played dumb. "I thought you liked him. He likes you, you know."

"Of course, I like him, Jess. But, I can't show up tomorrow with your eye looking like that! He's going to kill me!"

Jess pointed to his bruise as he kept his eyes on his phone. "This old thing? He won't even notice it."

"Jess-"

"Look, see." Jess read from his phone. "He says: Of course, Dean's sister can come. Say Hi to Dean." Jess looked up at Dean and waved one hand back and forth. "Hi."

"Jess, this isn't funny. I can't show up there with you looking like that! I'm serious. He's going to hate me! If I were him, I'd want to seriously hurt some freeloading asshole who hit my kid."

"Dean, I need the emotional support. He's expecting me to play nice with Lorelai. It's going to be painful enough for me even with you there, but it would be complete torture if I have to go by myself. But, you, you Lorelai likes. You can talk that boy-scout ass-kissing way you do to adults and keep Lorelai entertained. And with Clara along even better. If I remember correctly, that girl doesn't shut up. And neither does Lorelai so they'll hit it off perfectly!"

Dean sighed. "They already know each other from when I was dating Rory. Clara likes Lorelai."

"Even better. I'm serious here, Dean. You owe me for last night and I really need you there tomorrow. My preferred amount of dialogue at this event is to say hello to her when we get there and goodbye as we're leaving and let you and Clara provide all the entertainment in the middle. Sound like a plan?"

Dean looked scared to the point that Jess was starting to feel bad for him. "Look, Dean. To make you feel better, we can do one of two things. I can lie and say I walked into a door?"

Dean shook his head. "I don't want to make you lie to Luke. And, I'm a terrible liar. I'll be nervous, and I'll get all sweaty and look guilty."

"Fine, then I can text Luke now, give him a very sparsely worded rundown of what happened and tell him we're good and ask him not to bring up my eye tomorrow. Ok?"

Dean sighed. He knew he did owe Jess and that this was a relatively minor favor. Or would have been, without the bruise on Jess' eye. He would be looking forward to the lunch otherwise. "Ok. Do you think he really won't bring it up if you ask him not to?"

Jess shrugged. "I think if he's had time to process it and he knows I'm ok, he'll probably make some lame Luke joke about needing to separate us or us not learning our lesson after our fight at the party in high school, but he won't give you a hard time about if I ask him not to."

"You're sure?"

"I'm mostly sure." Jess said, expression serious. "I'm kidding, jeez. He won't do anything to embarrass you in front of your sister. Plus, he never believed that you actually started that fight in high school, so he'll probably think this was my fault, too." Jess searched Dean's face. "Seriously. I won't tell him, and you don't have to come if you really don't want to. I don't want to make you do something you really aren't comfortable with." Jess paused for effect. "Even though you did just punch me in the face last night." Dean's eyes narrowed, and Jess laughed. "Hey, just sayin'."

"All right, I'll come. And I'll bring Clara."

Jess held up his phone. "And text or no text?"

Dean sighed, rubbing a hand on the side of his head, which seemed to be pounding even more after talking to Jess. "Yeah, you should probably give him a head's up, so he won't be shocked tomorrow."

"Ok, hold on." Jess started typing. "And, don't worry, I'll emphasize the 'we got in a fight' aspect of the evening rather than going with the whole 'Dean got hammered and clocked me one out of nowhere' angle."

"Great." Dean said. "You really don't need to enjoy this as much as you are, you know?"

Jess feigned serious concentration while he thought about that. "Huh. I think I do."

Dean watched Jess stare at his phone, eagerly waiting for a response, when the phone buzzed to signal an incoming call instead. Dean's stomach, which hadn't been feeling steady to begin with, now felt like it was twisted in a knot. He really didn't want Luke to hate him. He would understand if he did. But, he really didn't want that to happen. He genuinely liked Luke and didn't want to lose that connection.

He listened as Jess picked up the call. "Oh, hey, Luke. What's new? How's Lorelai doing? Dean and I are really looking forward-"…."Uh-huh."…"Yep." Dean wished he could hear Luke's half of the conversation…."Yeah, we're both fine. And, we're all made up."…."No, I hadn't forgotten about it, I just didn't want to talk about it while I was at work"…"We've managed to go almost twenty-four hours now without swinging at each other and everything, just like good little boys."…..Jess smiled toward Dean. "I agree with you completely, Luke. This is no way for grown-ups to behave."…. "Yes, adults, sorry. Grown-ups is just a much more fun word to say."….."I'm not exactly clear on where you went wrong either, but I'm glad we can both agree on this incident being your fault." Jess cringed and held the phone away from his ear for a moment… "I was kidding, Luke, Jeez! You used to be able to take a joke. You're getting so serious in your old age. Either that or dating Lorelai might not be agreeing with you. You may want to consider-"…."Hey, I was just throwing thoughts out there-"….."Ok, I'm glad we got this all cleared up."…"Yes, never again. We promise."….."You have nothing to worry about here."…"Ok, yeah, text me the restaurant info."…."Ok, love you, too. See you tomorrow."

Jess pushed a button on his phone to end the call and turned to Dean with a smug smile on his face. "See? Everything's going to be fine. Luke just needs to yell a little when he's mad. Or surprised. Or scared. Or basically when anything happens that relates to me in any way. But, now he's got it out of his system and everything will be fine tomorrow. He won't make a big thing out of it at lunch."

"That didn't really phase you at all, did it?"

Jess shrugged. "It would have more before you moved in. But, honestly, I have so many brownie points with him right now for taking in your homeless ass, that I know he's not going to hold something this little against me."

Dean nodded. "Thanks, Jess. For taking in my homeless ass, and for working that out with Luke just now. You're a really good friend."

Jess smiled. "Hey, when you're right, you're right." Jess set his phone down on the counter. "I really need to pee. But, seriously, you don't look so good. You should finish that Gatorade and eat some of the Saltines. It might make you feel better." Jess clapped Dean on the arm gently as he walked past him into the bathroom.

Dean grabbed the Gatorade and walked over to the kitchen to look for the Saltines. He hadn't eaten anything all day, and he knew it was probably contributing to his nauseas. Dean paused in front of Jess' phone, listened for the sound of urinating coming from the bathroom, and quickly pushed the button to light up the screen. Jess' most recent message was still in view: 'Hey Luke, long story short: Dean and I kind of got into it last night. 85% my fault. We are good now, but I've got a black eye and wanted to warn you before you saw me tomorrow. Dean is still as pretty as ever. Can you please not make a big deal about my eye in front of Lorelai and Clara?'


	12. Chapter 12 - Lunch with Luke and Lorelai

**Chapter 12 Notes:** Luke and Lorelai have arrived in New York. Here's the first glimpse of Lorelai that I've written in a while. I think she's always tougher for me because I find her character so not relatable. As always, thanks to everyone who is reading my little story, and all reviews and feedback are warmly welcomed.

 **Disclaimer:** I own nothing except my own obsession with Gilmore Girls.

 **Trigger Warning:** Homelessness. Mentions of 'off camera' domestic violence.

Dean listened to his sister's story over the rattle of the subway train. He had met her at their aunt and uncle's house to take her into the city to meet up with Jess, Luke and Lorelai for lunch, followed by a trip to the science museum just the two of them. Dean had tried to mentally ready himself for a run-in with his uncle on the train ride out to their neighborhood and he had been relieved to not have to deal with Mel when he had arrived. His aunt had opened the door and barely had a chance to hug him and say hello, when Clara, jacket and hat on and ready to go, had barreled past her to hug Dean, excitedly pushing him out the door with her while she yelled goodbye to her aunt.

Dean had brought up his uncle once they were seated on the subway. He didn't want Clara to be worried about them meeting and feel like she had to run interference or rush out before his uncle knew Dean was there. He didn't want his situation with his uncle to put any extra weight on her twelve-year old shoulders. He tried to sound more confident than he felt when he told her that he wasn't hiding from their uncle and if they ran into each other, he could deal with it. Clara has listened attentively to everything Dean had told her. Quietly, without interrupting, which should have been his first clue that something wasn't right. When he asked her if she understood, he had been surprised to see her tear up.

Dean had put his arm around her and asked her what was wrong. Clara had told him about the fight she had overheard between Mel and Gretchen when Mel had returned home the night Dean had visited. Dean had listened through the parts where Clara heard Gretchen telling Mel that what he had done to Dean wasn't right, both kicking him out in the middle of the night and throwing out all his possessions. It was the first time that Clara had heard their aunt raise her voice in anger. Their uncle hadn't seemed as worked up and Clara had had trouble hearing his end of the conversation. Her aunt had said they had an obligation to care for Dean, and they had failed him terribly. The argument had gone on for several minutes, with their aunt comparing Dean to Kevin and asking what Mel would have wanted his sister and brother-in-law to have done for Kevin if the situations had been reversed and telling him he should apologize so that Dean would come back. At one point, Clara had heard their aunt tell their uncle not to touch her. At another, Clara thought her uncle had said something mean about Dean because she heard the laugh he always used when he was putting someone down followed by their aunt saying there was nothing funny about this situation. Then their aunt had thrown their mother in their uncle's face, something along the lines of what would Jen think about what you did to her son, and then answering her own question by telling him that if his sister knew what he did, she would never forgive him. She would be disgusted with him. That's when Clara had heard a loud slap, followed by a gasp from her aunt, then crying, and then soft murmuring from her uncle.

Dean had pulled Clara close against his side as he listened to her story. When she finished, he shifted in his seat and took hold of both of her shoulders, forcing her to look at him. "I'm so sorry that happened, Clara. I'm sorry that Uncle Mel is such a jerk, and I'm sorry he hit Aunt Gretchen. And I'm so sorry you had to hear that." He paused to collect his thoughts. "If anything like that ever happens again. Or if he ever hits you. Or ever even threatens to hit you, I want you to call me at Jess' number, ok? Right away. Do you understand me?"

Clara nodded, her tear streaked face making Dean's heart clench. Dean really hoped this was a one-time occurrence, for his aunt's sake as well as his and Clara's. He thought about what he would do if he ever got a panicked call from his sister. Would he actually call the police on his uncle? Should he already call the police on his uncle because of this incident? He didn't know. He hoped nothing like this ever happened again, so he would be saved from making that decision, but at the same time, he wondered if something like this would help him when he was ready to try to get custody of Clara.

Dean released Clara's shoulders and pulled her against his side again, wrapping her small body in a one-armed hug. He dug a tissue out of his pocket and handed it to his sister and watched her wipe at her face, her crying tapering off to a few sniffles. "Are you still feeling up to going to lunch with Jess and his uncle and Lorelai. If you're not, we can swing by the restaurant and I'll explain that we're going to do our own thing instead. They'll understand."

Just when Dean was getting comfortable with the idea of skipping what would likely be a very uncomfortable meal, for him at least, Clara started shaking her head. "No, I want to go. I want to see Lorelai and Jess."

"Ok, if you're sure."

"Yeah, it'll be fun. Remember how much fun Lorelai is, Dean?"

Dean nodded, watching a smile grow on his sister's face. The few times she had met Lorelai, Clara had found her very entertaining. "I remember."

"And remember when we went to the winter carnival with Jess and Rory and Jess kept saying funny stuff? Like pretending he was all annoyed when he was really being funny?"

Dean laughed softly, and then borrowed one of their dad's favorite phrases. "Hmm…I have to really quint to see that one."

Clara giggled. "I think the two of them will be really funny together, don't you think?"

"Oh, I have no doubt."

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Luke pulled into an empty parking spot in the public parking garage and put the ticket he had been given face-up on his dashboard as instructed. He was still mentally figuring out what the cost of parking would come out to based on the posted rate per fifteen-minute increments and the time they expected to spend at lunch and at the show.

"You really hate the city, don'tcha?" Lorelai asked playfully from the passenger seat. He was embarrassed that he had let his expression register his discontent. He was out on a date with his girl. He wanted to show her a good time and be good company, not get caught up in the frustrating minutia of being in New York.

He looked over at his girlfriend, devilish smile on her beautiful face, and thought, not for the first time in the past few months about what a lucky bastard he was.

"Want to know what tipped me off?" She cocked her head to one side and Luke, never being able to resist the look in her eye when she was about to tease him, leaned in to kiss her. Then pulled back to look at her.

"Do tell."

"Well, you cursed like a sailor on the expressway. Then you complained like a grumpy old man about the bumper to bumper traffic once we got _off_ the expressway. Then you really didn't seem to enjoy the quest for a garage that wasn't full, and now you don't look too happy because you've realized we're going to end up spending around forty bucks on parking now that we've found a spot. After putting those clues together to form a pattern a la Sherlock Holmes, I've deduced that Luke hates the city!"

Luke smiled at her. "That may be true most of the time, but today there is no where else I'd rather be."

"Is that so?" Lorelai smiled and scooted closer to Luke. "Does it have anything to do with your present company?"

Luke kissed her again. "My present and future company. Today the city is where my girl and my favorite nephew are. And lucky me, I get to see both of them at the same time. What could be better than that?"

"Um, let me see…..Oh, wait, was that a rhetorical question?"

Luke's smile faltered a little. He knew Lorelai was only joking, but it still hurt him a little every time she made a comment about Jess that he would never make about Rory. He really wanted them to be ok with each other, to more than get along and actually like each other.

"You're going to keep an open mind, right?"

Lorelai nodded seriously. "The openest. I promise."

"He's really matured a lot since you knew him. He's different now. He was always a good kid, deep down, but now, he's gotten over his whole surly teenaged attitude."

"So, you keep telling me."

Luke knew he needed to put in the effort if he wanted Lorelai and Jess to get along, but he felt a twinge of resentment at the way he often felt like he had to defend Jess to Lorelai. He really hoped there was a payoff to this someday. He tried to picture he and Lorelai happily married somewhere down the road. He could easily see himself being in Rory's life as her stepfather, helping her with dad things like car maintenance, carrying furniture when she moved, and fixing things that broke in her apartment, maybe walking her down the aisle one day if Christopher couldn't be bothered, throwing himself in front of a bullet or speeding train that was headed her way if the situation called for it, and someday being a real grandpa to her kids. As much as he tried to imagine the relationship between Lorelai and Jess evolving similarly, he always got stuck when he tried to picture the details of what that would look like.

It dawned on him that he should probably warn Lorelai about Jess' eye so that she wouldn't make a snarky comment about it and set Jess off. He wanted to at least give this lunch a fighting chance.

"Oh, I want to tell you something before we go so that you won't be surprised. I talked to Jess last night and I guess he has a black eye right now."

Lorelai nodded seriously. "Uh-huh. Are we getting to the surprising part anytime soon?"

Luke sighed. "Lorelai."

"Oh, I get it, the black eye _was_ the surprising part!"

"Yes, it was. Anyway, I guess he's sensitive about it because he made me promise not to make a big thing about it today when I saw him and I just wanted to let you know so you wouldn't be caught off guard and say something about it. I think he knows he's too old for stuff like this, fighting and everything, so he's embarrassed about it."

"My lips are sealed. Am I allowed to give the black eye silent but judging looks?"

"If I say no is it really going to stop you?'

"So, do we know how said hooligan got said black eye?"

"Yeah. I guess he and Dean got into a fight a couple of days ago, and things got a little ugly."

"Dean gave Jess the black eye? That doesn't sound like Dean?"

"That's what Jess said happened." He was feeling a little defensive about Jess and wasn't going to volunteer that Jess had told him the fight was mostly his fault. "He says they're made up now, though, and things are good between them again." Luke shrugged. "I guess stuff like that can happen when two people are sharing such a small space."

"I guess." Lorelai echoed. "Though Dean never got into fights before Jess moved to Stars Hollow. And now he's been in two, both with Jess."

"So? What's your point? Jess has only been in two fights since he moved to Stars Hollow, too, and they were both were with Dean?" Luke wasn't counting the swan since it had attacked Jess unprovoked. Plus, he had kept his word to his nephew and never told anyone about that.

Lorelai let out a short laugh. "That you know of."

"Hey, the last time Jess had a black eye it wasn't from getting into a fight." Luke felt himself getting annoyed.

"I know, I know, he got Marsha Brady'ed by a football. I've heard the explanation."

"Then what are you implying about Jess getting into more than just that one fight with Dean at that kid Kyle's house?"

"Just that you're really out of the Stars Hollow gossip loop! Or were, past tense, before you had a super in the know girlfriend to clue you in to the goings-on in the seedy underbelly of Stars Hollow."

"Jeez, Lorelai, you make it sound like Jess was running some illegal fight club. He was an angry kid. He had a lot of reason to be, growing up the way he did. If he got in more fights than the one with Dean, I don't know about them and I don't want to." "We should go."

"Ok." Lorelai was looking at Luke carefully.

They got out of the truck and Luke walked around to meet Lorelai on her side, taking her hand in his. He wanted to get back into date mode and away from the topic of Jess' past misconduct. "I'm really glad we're doing this, Lorelai."

"Me too." She leaned up to kiss him quickly, a smile on both their faces as they parted and started walking toward the garage elevator. "So, you're really not going to say anything about his eye? You, Luke Danes, who loves to give people you care about unsolicited advice when they engage in behavior you don't approve of? That Luke Danes isn't going to make a quote unquote 'big thing' about his nephew having a black eye?"

"That's right. Jess is an adult and I'm going to respect his wishes that we not talk about it."

"Oh, really?"

"Yep. He's nineteen and lives two hours away, it's not like I can ground him or send him to bed without dinner for fighting. He's grown. He doesn't need my what did you call it, unsolicited advice, on how to run his life. I'm just going to let this go."

"How zen of you."

"That's right." Luke smiled. "Zen is my middle name."

"Luke Zen Danes. It has a nice ring to it."

"Yes, it does." Luke looked at Lorelai, swinging their joined hands back and forth idly as they walked. "Plus, I already yelled at him for about ten minutes on the phone last night." Luke smiled at Lorelai's laugh, thankful that the conversation about Jess hadn't derailed the mood.

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Jess was cold. He felt stupid for being cold. He should just go inside. He knew he was being a child. He wished he had gone with Dean to pick up Clara so they could have all arrived together to minimize how much he would have to interact with Lorelai. Five felt like a safer number than three. He could see Luke and Lorelai through the window, holding hands and talking as they waited behind two other couples at the hostess stand. When it was their turn, Jess watched Luke speak to the hostess. The hostess said something back with a big customer service smile on her face. Lorelai replied, and Jess watched Luke laugh and look adoringly at Lorelai while the hostess' smile turned to a confused and slightly uncomfortable expression for a moment. Lorelai must have made one of her annoying comments that she seemed to believe made her look sharp and witty instead of just desperate for attention. Jess sighed. He really didn't want to go in there by himself.

Luke and Lorelai turned to follow the hostess into the dining room and Lorelai and Jess' eyes met through the window. Lorelai's smile dimmed for a beat and she turned to Luke, putting her hand on his arm as she spoke to him. Luke looked toward the window, and a big grin spread across his face as he spotted his nephew. Luke waved and Jess raised a hand and waved back, trying to force a smile onto his face, but knowing he was probably failing miserably. Luke said something to the hostess who nodded and returned to her podium to address the next group of people. Luke, still grinning, looked back toward Jess and motioned for him to come in. Jess sighed and headed toward the entrance of the restaurant.

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Jess walked into the foyer of the restaurant. Luke and Lorelai were waiting for him off to the side, out of the way of the hostess. "Hey."

"Hey, Jess!" Luke gave Jess a quick hug, not wanting to embarrass the boy in public, but unable to resist altogether. When he pulled back, he gently cupped Jess' jaw under his bruise and turned his face slightly to get a better look at his eye. "I don't like this, Jess. You guys are too old to be doing this kind of crap. Especially to each other, now that you're friends."

Jess nodded, and Luke released his face. "I know. You're right."

"It's really good to see you, kid."

A small smile formed on Jess' face. "You too." Luke took a step back and Jess turned to Lorelai. "Hi."

"Hi Jess. I guess some things never change, huh?" Lorelai said.

Jess felt himself involuntarily tensing. He tried to will himself to relax, but he could already feel himself shutting down and a wall going up. "Guess not."

The hostess approached them then, said something to Luke and they followed her into the dining room to an oversized booth. Luke and Lorelai sat on one side and Jess sat down on the other. He had to force himself to stay positioned in the middle of the bench, equidistant between his uncle and Lorelai, instead of scooting all the way down the booth to sit against the wall where he would be directly across from Luke and could pretend Lorelai didn't exist.

"So, what's new, Jess? Other than your pretty face?" Luke asked. He laughed at the stink eye Jess gave him. "I know, I know. I'm not going to make a big deal of it. How's everything going? How's work?"

Jess sighed. "Work's fine." He refused to share any personal details of his life and put them out there to be mocked by Lorelai. "It's a job. I can't complain. How are things at the diner?"

"Good. Caesar says hi." Luke said.

"I think Caesar misses you." Lorelai said.

"Oh, yeah?"

"Yes. Lane is working there now, and she's really whipping that place into shape, isn't she, Luke?"

"Oh, yeah." Luke agreed. "She's very efficient. I think Caesar's a little scared of her. She kind of yells a little when she has to wait too long for an order. She keeps Caesar on his toes. It's pretty funny to watch." Luke laughed, and Jess smiled.

"Not cool, Luke." Jess feigned admonishment. "Have some loyalty. Caesar's been with you forever. Who knows how long Lane is going to stick around?"

Luke was still chuckling. "You're right. I just can't help it. You should see them."

Jess turned to Lorelai, feeling the need to prove he could interact with her like an adult. "How are things with you, Lorelai?"

Lorelai grinned. "Things are great with me. The Inn is up and running. Business is good. And, of course, Rory is great. She's at Yale."

"So, the rumors are true." Jess said.

"Yes. And, she's loving it there. She's finally surrounded by people as smart as she is. Or, almost as smart, but I'm biased, after all." Lorelai smirked. "She's doing great in all her classes. And she's started dating this guy at Yale that she's really excited about." Jess kept his eyes locked on Lorelai's as she spoke, determined to not flinch or look away as he listened to how perfectly everything was going for Rory. "He's very smart and ambitious from what I hear. It's just so great that she's found her tribe, so to speak, at Yale. I feel like the world is really opening up for her now, and she's starting to realize she can do anything. I'm loving seeing her so happy."

Jess noticed the puzzled look on Luke's face. "It this still that Marty guy? I thought Rory wasn't that into-"

"Oh, look who it is!" Lorelai said as Dean and Clara walked up to the table. She stood up and enthusiastically hugged each of them, as they exchanged greetings.

As Luke slid down the booth to follow Lorelai out and greet Dean, he tapped Jess' arm and caught his eye, smiling warmly at his nephew. Jess gave him a wary smile in return, his spirits lifting a bit at knowing Luke appreciated his efforts.

Jess stayed seated and watched Luke greet Dean and pull him into a quick hug, then extend his hand to Clara who shook it seriously. He was glad he had told Luke the fight had been his fault. He knew Dean liked having Luke in his life and he was glad he hadn't damaged their relationship. He knew ultimately that if Dean was serious about wanting to get custody of Clara, that Luke could do more to help him with that than he ever could.

"Hi, Jess!" Clara greeted him as she scooted in next to him in the booth, after Luke had made a joke about Clara needing to sit in the middle to keep Jess and Dean separated.

"Hi, Clara. How's it going?"

"Do you remember me from the winter carnival that time? I was there with Dean and you were there with Rory."

"I remember you. You're hard to forget."

Lorelai smiled. "Rory and Jess together at the winter carnival. Wow, that feels like forever ago!"

"Really?" Dean asked. "It feels like just yesterday to me. God, I couldn't stand Jess back then." Dean caught Jess' eye over Clara's head and smiled good-naturedly.

"Really?" Jess feigned confusion. "Huh. I could never tell. You were always so polite and friendly to me and kept your feelings under control so well." Luke and Dean laughed at Jess' sarcasm.

"Well, I definitely remember all the tension between you two." Lorelai said. "So, how did this happen?" She moved her hand vaguely back and forth between Jess and Dean. "This whole buddy-buddy situation you've got going on here?"

"Oh, well, I needed a place to stay and Jess let me stay with him. He pretty much saved me. I don't know what I would have done otherwise." Dean said.

"No, I mean, I get that you needed a place to stay, but you had other friends from high school. Why didn't you stay with one of them? I can't wrap my brain around the new dynamic I'm witnessing. It feels very surreal seeing you two as friends. Like I'm watching some kind of crazy never-before-seen episode of the Twilight Zone. What made staying with Jess, of all people, seem like a good idea?"

"Uh, I guess none of my other friends offered. Jess did." Dean said. "And it was weird at first, sure, but I'm glad I ran into him and that we got to know each other. Jess has really been there for me. He's one of my closest friends now."

"Aw, stop, Dean. You're going to make me get all emotional." Dean laughed, and Jess smiled.

Clara giggled and turned to Dean, her thumb up like a hitchhiker, pointing in Jess' direction. "See? I told you I remembered him being funny."

Dean smiled. "He has his moments."

"Huh." Lorelai said. "This is all very strange and interesting."

"What's so strange, Lorelai?" Luke asked. "They're both good kids. They got over their differences and became friends. It happens all the time."

"Hmm. Got over their differences, did they? I think Jess' black eye begs to differ."

Clara looked puzzled. "What do you mean?"

Lorelai looked uncomfortable at what she said, not having realized that Clara didn't know about the fight. "Oh, um, I just-"

"It's ok, Lorelai." Dean cut in and turned to his sister. "Jess and I got into a little argument a couple of days ago, and it got a little out of control and I'm the one that gave him the black eye." Dean was aware of the terrible timing of this admission. He hoped Clara wouldn't see him the way she saw their uncle. "It was a stupid thing to do. It was wrong of me to hit him and it's never going to happen again."

"Oh. Did you hit Jess because he hit you first?" When Dean didn't answer right away, Clara turned to Jess, trying to make sense of her normally non-violent brother physically attacking a person he called a close friend. "Did you hit Dean first?"

"Uh, not exactly."

"Did you hit him at all?"

"Uh, not really. It was all over pretty quickly." Jess glanced across the table to see confusion on Luke's face and disbelief on Lorelai's.

Clara pushed at Dean with her hands. "Move, Dean! Get up! I need to go to the bathroom."

Dean obliged. "Clara are you all right?"

"I'm fine!"

"You want me to come with you, Clara?"

"Don't be stupid! You can't go to the girls' bathroom, Dean!" Jess saw the waitress moving behind Dean, getting almost to their table and swerving off at the last minute once she registered that this wasn't a good time to approach.

Lorelai got up, too. "Is it ok if I join you?"

Clara nodded. "Sure, Lorelai."

Dean sat back down and put his elbows on the table and rested his head in his hands.

"What was that all about? Is she ok?" Luke asked. "Are you ok, Dean?"

Dean lifted his head to find Luke and Jess staring at him. "I'm sorry. She's upset because….the night I went over there…." Dean sighed. "I guess after I left my aunt and uncle got into an argument. My aunt was telling my uncle that it had been wrong to throw me out in the middle of the night and to throw out all my stuff."

"Your uncle threw out all your stuff?" Luke asked.

"Yeah, after he kicked me out he gave everything I owned to Goodwill. And, I guess, when they were fighting about me…Clara heard my uncle hit my aunt. And my aunt crying. And, I don't know what to do. And, now Clara probably thinks I'm just like him because I did the same thing to Jess."

"God, Dean. I figured your uncle had to be a real prize for throwing a kid out like that in the middle of the night, but this is…wow, this is so much worse."

Dean looked at Luke, with tears forming in his eyes. "What should I do? She hated it there even before this. My uncle is such a jerk. I really want to get Clara out of there. She wants it, too. I really want to get custody of her, but I feel like I have so many things in my life to put in order first. I need another job, maybe two more. I need to get an apartment. I don't know how to do any of this." Dean wiped away a tear that started sliding down his face. He didn't want his sister to come back from the bathroom and see him like this.

"This might change everything. I think you need to see a lawyer." Luke said.

"What do you mean?"

"I'm just saying. If your sister is in an unsafe environment, it might be easier than you think for you to get custody of your sister."

"What about Nicole?" Jess asked. "Maybe she could help or would at least know someone who could."

"That's a good idea, Jess. Nicole did business law, but there was a department for everything at her firm. I bet she could put you in touch with someone who does this kind of stuff."

"Who's Nicole?" Dean asked.

"She's Luke's ex-wife." Jess answered.

Dean waited patiently for some sort of punchline. "Wait, seriously?"

"Yeah." Luke admitted reluctantly. "It was a very short-lived marriage. It wasn't right from the start."

"I agree. I always knew Nicole could have done better. I mean she was a lawyer and everything. 'Nuff said, right?" Jess said.

Luke turned to Jess. "I think he gets the picture, thanks."

"I don't know. There's no way I can afford a lawyer."

"If you meet with Nicole and she can help you, or she finds you another lawyer who can, I'll pay for her services. Don't worry about that. Your little sister should not be living with an abusive man, Dean."

"I know. I know. You're right, Luke. I just don't know how to do any of this. And, I don't even know if she still wants to live with me after what I just told her."

"What? That you got in a fight with Jess? That's not the same thing as what your uncle did. Not by a long shot. And even if you threw the first and only punch, Dean, I get how someone can work your last nerve until you explode. And, yeah, maybe you need to work on your self-control, but it seems like Jess is the only person who triggers you to violence like that. And, I can't say the concept is completely foreign to me. I love Jess like he's my own, but I understand how good he is at pushing your buttons when he wants to. I once pushed him into the lake in Stars Hollow because I snapped and couldn't take any more of his attitude. I'm not proud of that."

Dean watched Jess studying the table top in front of him, and knew he had to come clean about what happened. "Luke, that's not what happened. Jess didn't push me. He didn't do anything wrong. I know he told you that the fight was his fault, but it wasn't. I was upset about my uncle throwing out my stuff. I stole a bottle-"

"Dean, stop, it's fine."

"It's not fine, Jess. I stole a bottle of alcohol from my uncle's house. I got pretty trashed on the subway ride home. I woke Jess up and he was really nice to me, even though I was a drunken mess. We talked for a while and then something happened, and I don't know. I got confused and I somehow thought Jess had thrown out my stuff at his apartment while I was at my aunt and uncle's and I flipped. I cornered him against the wall. I said all this really mean, terrible stuff to him, and when he said one thing back to me, I lost it and punched him. It was the middle of the night, and I didn't think I deserved to stay there anymore, so I was going to leave, just walk out drunk with no plan in the middle of the night. And, Jess, even after what I did, Jess wouldn't let me. He pulled me away from the door and told me to just go to bed and we'd work it out in the morning. I was so terrible to someone who's been so good to me. I am like my uncle. And, I am so sorry, Luke. I'm so grateful for everything you've done for me and I totally get it if you hate me now." Dean felt more tears running down his face and wiped them away.

"Dean. Hey, Dean." Luke reached across the table and grabbed Dean's bicep, giving him a little shake. Jess saw the waitress start toward their table again, only to veer off when she saw Dean crying. They would never get to eat at this rate. "Dean, c'mon, kid. Look at me." Dean obeyed. "I don't hate you, Dean. I admit I had a momentary urge to put you in another headlock like when you broke up with Rory." Dean huffed out a quiet laugh. "But, I don't hate you. You're going through a lot. You're under a lot of stress right now. I get that people make bad choices when they're under stress. If Jess can forgive you and move on, then so can I. Ok? We still friends?"

Dean nodded. "Yeah, we are. Thanks, Luke. Thank you so much for not hating me"

"It might be a good idea to not drink any more-"

Dean nodded fervently. "Yes. I already promised Jess I wouldn't drink again while I was staying with him. I'm just so sorry."

"Ok. How about you promise me not to drink until you're twenty-one and it's, you know, actually legal?"

"Yes. Yes, I promise. No more drinking until I'm twenty-one. I swear."

"Good man. Ok, Dean. I meant what I said about helping you pay for a lawyer or for anything else you need to get custody of your sister. Ok?"

"Thanks, Luke, but I couldn't ask you to do that."

"I didn't hear you ask. I heard myself offer. Jeez, you listen just like Jess."

"No way. His listening skills are way worse than mine." Jess said, getting a chuckle from Dean.

"I'm going to call Nicole tomorrow and ask for her advice. If she thinks she can help or if she knows someone who can, I'll give her Jess' number to contact you. Ok?"

"Ok, Luke. Thanks. And can you please not mention any of this in front of Clara? I don't want to get her hopes up until I know whether or not it's realistic for me to ever get custody."

"Sure thing, Dean."

Dean wiped his eyes with a napkin and got himself looking presentable just as Lorelai and Clara approached the table, smiling and holding hands.

Lorelai grinned as she took her seat. "What did we miss? What were you fellas talking about while the girls were off powdering their noses?"

Clara giggled cheerfully, as she climbed over Dean to reclaim her spot between him and Jess. Jess looked on in confusion, puzzled at how a few minutes alone with Lorelai could have had such a positive impact on the girl's spirits. Someone who could do that for a hurting child couldn't be all bad. Maybe there was a good side to her that he needed to work harder to see. Jess turned to Lorelai. "We were just talking about Nicole. You remember her, right? The beautiful attorney that Luke was married to? The very smart and ambitious one?" Oh, well. He'd work on seeing the good side of Lorelai next time.

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The rest of lunch passed uneventfully. Once the screaming and crying had died down, the waitress had approached their table and taken their orders. Friendly conversation was made, mostly between Lorelai and Dean, and Lorelai and Clara, and Luke and Dean. Jess had to admit that Lorelai was good at including Clara and bringing up topics the girl was interested in. Lorelai had the best social skills at the table, when she wasn't being a jerk and rubbing Rory's new boyfriend in his face. Luke was more awkward with children. He made efforts to talk to Clara, but they seemed to end with her cracking up even when Luke wasn't trying to be funny. Now that Dean and Clara were there to distract Luke and Lorelai, Jess let himself fall into the observer role, as he tended to do in groups. He ate his meal and watched quietly, participating in the conversation when asked a direct question, or when Luke or Dean said something that was begging to be lovingly mocked. Jess appreciated his uncle as he watched him with Lorelai and with Dean and Clara. A part of him toyed with feeling jealous of Luke's new attachment to Dean, but he was mostly just grateful that Luke was who he was, someone who was always willing to help someone he knew, no matter how tangentially, because he was just that kind of person.

Outside the restaurant, after Dean and Clara had headed off to the science museum and Lorelai had run back inside to use the bathroom, claiming she had drank too much water and didn't want to risk waiting in the long line at the theater, Luke said goodbye to Jess. He pulled his nephew into a hug. "I love you, and I'm so proud of you, Jess. I hope you know that, kid." He pulled back and put his hands on the shoulders of Jess' jacket so he could look the boy in the eye. "I couldn't be more proud of how good you've been to Dean, helping him like you've been doing. It sounds like he was really lucky to have you for a friend the other night. I'm proud of you for not hitting him back. And, for not letting him leave your place drunk like that, even when you had to have been pretty pissed at him. That was very mature, Jess." Luke smiled. "You're becoming a real grown-up, kid."

Jess laughed softly. "Small steps. First, I'll master being a grown-up, then I'll work on being an actual adult."

"Sounds like a plan. And I know you didn't want to cause more trouble for Dean when you sent me that text that said you guys got in a fight and that it was, what did you say, seventy-five percent your fault."

"Eighty-five percent. I was being generous." Jess averted his eyes from Luke, knowing what was coming.

"Sorry, eighty-five percent." Luke dipped his head down, trying to make eye contact with his nephew. "I don't like you lying to me. Am I really such a jerk that you didn't think I could understand? Did you think I was going to yell at Dean?"

"In my defense, you did yell at me on the phone when you thought I started the fight."

"Yeah, well, you're mine to yell at, kid." Luke smiled. "I wouldn't have said anything to Dean about it if you had told me the truth and asked me not to. You know that, right?"

Jess nodded. "Yeah, he was just so nervous about seeing you, and having you hate him." Jess shrugged. "I just thought it was easier this way. For everyone."

"It's never easier for me if I know you lied to me, Jess."

"I get it. I'm sorry. I won't lie to you again." Jess smirked. "Do I need to start crying and begging you not to hate me for you to take my apology seriously? 'Cause I'm game if that's what you need."

Luke smiled and cuffed Jess lightly on the back of the head. "Don't be an ass, nephew." Jess smiled back.

Luke patted Jess on the shoulder and withdrew his hands putting them in the pockets of his jacket. He watched Lorelai through the window, as she made her way through the foyer of the restaurant to the door. He chuckled quietly, already anticipating the drive home after the show when he could tell Lorelai that Dean had confessed to starting the fight while she was in the bathroom and that Jess had behaved like a responsible and upstanding adult.

"What's so funny?"

"Nothing, nephew. I'm just happy."


	13. Chapter 13 - Dewey, Cheetum & Howe

**Chapter 13 Notes:** Nicole guest stars in this chapter. This may be her only appearance or she may pop up again in small roles, but there will be no current Luke/Nicole relationship, only mentions of their past. In this story, Luke was briefly married to Nicole, as on the show, but she never cheated on him. The marriage just ended because they realized it should never have happened. Her cheating on Luke and the accompanied fight in front of the diner/I'm not wearing my socks/car kicking incident never made sense to me and always seemed both out of character and poorly contrived as a way to get Luke out of an awkward plot situation leaving him the 'good guy' and Nicole the 'bad guy' even though he was the one who never fully committed to that relationship or to moving in with her. I liked Nicole's character, not to replace Lorelai as end game for Luke, but as a smart and attractive woman who seemed to have her shit together. I feel like the end of her story arc did not do her character justice. All reviews are welcome and greatly appreciated. :)

 **Disclaimer:** I own nothing except my own obsession with Gilmore Girls.

 **Trigger Warning:** Homelessness. Mentions of 'off camera' domestic violence.

Nicole wasn't usually caught off guard at work. She took her job seriously. Prepared well for every case she worked on and every client she dealt with. It was rare for her to feel as blindsided as she did at the moment, sitting at her desk, phone to her ear, listening to the receptionist asking her if she can put a call through.

"Nicole? Are you still there?"

"Sorry, Robin." Nicole said. "Yes, I'll take the call. Thank you."

"Sure thing."

Nicole took a calming breath as she listened to the click on the line. "Nicole Leahy."

"Uh, hi Nicole. It's Luke. Uh, Luke Danes?" Nicole smiled as she listened to her ex-husband phrase his own name like a question. She had always found his humble and bumbling nature endearing in a small town Mayberry kind of way. She couldn't decide how friendly she should let herself come across since she wasn't sure what to expect, so she put on her best professional demeanor before speaking again. Not her aggressive, asserting herself in court level of professional. She aimed for neutral and no-nonsense, but still pleasant.

"Yes, Luke. I know who it is. What can I do for you?"

"Oh, uh, sorry. I'm calling about a legal issue, I guess. I have a friend with a legal problem and I wanted to see if your firm was somewhere he could go to get help with his problem. He doesn't know how to go about it, and well, I don't either, and you were the first lawyer I thought of. The only one I know really." There was a beat of silence. "I hope it's ok that I called…. Is it?"

Nicole felt an old hurt as the events of the summer came rushing back to her. The impromptu wedding on the cruise ship only a few months into their relationship. Realizing their mistake and trying to return to just dating. Luke never fully committing to being with her. Not the way she wanted. Her pulling the plug when tolerating his obvious lack of love for her started to feel pathetic. And explaining the whole embarrassing situation to her friends and family. She sighed. "It's ok that you called, Luke."

"How have you been Nicole? You doin' all right?" Nicole could hear the hesitance in his voice. She knew he was thinking about whether it was an appropriate question to ask. She wasn't sure herself.

"I'm fine, Luke. I've had better years, but I'm doing ok. How are you?" She was nothing if not polite.

"I'm ok." "Uh, Jess came home."

Nicole smiled at that, allowing it to color her voice. "That's great news, Luke. I'm really happy to hear that." She had felt terrible for Luke when his nephew had taken off without a word. She knew how much Jess meant to him and that the loss he had felt at Jess' departure had been one of the main catalysts for his premature proposal and desire to immediately be part of a family. It had been so clear to her after the fact. She still wished she had been more aware that night on the deck of the cruise ship. "Is he all right?" She knew she was being more transparent with her concern than what was appropriate for a business call with a potential client. "Is Jess who you're calling about? What happened? Does he need a criminal defense attorney? That's not something we handle here, but I know some real killers I can set you up with."

"Oh, uh, no, it's not Jess. Jess is actually doing ok. He's living in the city. Has a fulltime job and his own tiny little studio apartment." Nicole could hear the warm smile in Luke's voice as he talked about his nephew. "And, I mean, really tiny. Like barely fits his mattress tiny…but, he's stable. He's doing ok. He's good."

Nicole allowed herself to smile. "That's great, Luke. Really. I know how much he means to you and I'm glad you have him back."

His voice sounded off when he responded. "Thanks, Nicole. I appreciate that. And your concern for Jess. I appreciate that, too."

"Of course. I always liked your nephew." Nicole recalled dinners in Luke's apartment with him and Jess, and all the times she had run into the boy in the diner. She knew he had a reputation as a troublemaker in their small town, but he had always seemed like a fairly normal teenager to her. He had always been respectful to Luke and pleasant to her. It had only taken one conversation with Luke about Jess' mother for her to realize the defensive attitude he aimed at the majority of people in town was really a coping mechanism developed by a hurt little boy.

"I know you did."

Nicole smiled. "I know he was supposed to be the town delinquent, but I never felt like that little town of yours really gave him a chance. I always felt like Jess was basically a good kid."

"Thanks, Nicole. He is, really."

When Luke didn't continue, Nicole went back into professional mode and prompted him along. "So, if Jess is ok. Who are you calling about?"

"Ok, so here's my situation." Luke launched into telling Dean's story from the death of his parents to his uncle kicking him out to his time on the street and reconnecting with Jess in New York.

Nicole was taking notes. This wasn't something she would handle, but she wanted to have the facts when she turned it over to one of the junior associates in the family law practice. "Wait a minute…..Dean Forrester. Why does that name sound familiar?"

"Oh, uh, he was the kid that Jess was always fighting with, over Lorelai's daughter. Jess stole her from Dean. Dean tried to win her back. That kind of thing. He's the kid Jess got into that fight with at that party the weekend we were supposed to go on that ski trip."

Nicole reflected on this. "Jess took in his homeless high school nemesis? That's very nice of him. I'd say he's doing better than good, Luke. You must be really proud of him."

"I am. Really. I'm so proud of him. He's just becoming this really great almost adult, you know? It makes me so happy to see him finally showing other people what a good kid I always knew he was…"

Nicole felt a twinge of sadness even as she was happy for Luke. "Ok, so back to Dean's case."

Luke went on to describe how Dean wanted to get custody of his sister but didn't know how to go about it. He relayed what he knew about how Dean's uncle had treated him, throwing the boy out on the street in the middle of the night, getting rid of all his clothes. And he finished with Clara's story about hearing her uncle hit her aunt.

"And what's his uncle's name? You said he was a lawyer and I just need to make sure there's no conflict of interest. If there is, I can still set you up with a referral, we just couldn't take his case here."

"Oh, I actually texted Jess for it yesterday. I thought about that, too. He works in the city, and I thought it might be awkward if he worked at your firm or something. It's Mel, uh, Melvin Turner."

Nicole sat bolt upright in her chair. "Mel Turner? As in Melvin Turner of Horvath, Turner and Myers?"

"Uh, that's his name. I know he's a partner at his firm, but I don't know the name of it. I can check with Dean to find out?"

Nicole's head was spinning. Mel Turner hits his wife. It felt like an early birthday present had fallen into her lap. Mel Turner was one of the most despised lawyers her firm had the displeasure of dealing with in court. He was ruthless, underhanded, slimy, condescending and misogynist. And he always won his cases. The chance to publicly embarrass him over an unsavory aspect of his personal life, especially one as scandalous and potentially criminal as this, was too good to be true. Any firm in the city would want this case. Nicole could already picture the accolades she would receive from the partners for bringing in this case.

"I think we can help Dean." Nicole was grinning broadly now, glad she had taken the call. "We can take the case pro-bono because of Dean's financial situation. I can get him a meeting with the partner in charge of the family law practice, Raina Kline. She's a killer."

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Jess was sitting on his mattress, pillow propped up against the wall behind him as he typed on the keyboard of his laptop. He was working on the same story he had been editing for a while. He knew it was close to being done, but he was dragging his heels on finally finishing it. He had no idea what to do with it once it was done. It was longer than a short story, but it didn't feel long enough to be a novel. And even if it could fit into one of those categories, length-wise, he had no idea if it was anywhere near good enough to be published. He had written it because he felt like he had needed to. The characters and scenarios had popped into his head and hadn't left him alone until he had gotten everything out of his system and written down. The process had felt good, fulfilling even. But now that he was almost done, he had no frame of reference for how the effort he had put into this story, or his writing in general, could possibly factor into his life in any real way. He was still just a Kinko's employee, who holed up in his cramped little studio apartment, writing stories that had a good chance of never being read by anyone else. He had to wonder whether he was wasting his time.

He could admit that one reason he enjoyed the writing process so much was the escape it provided from his own reality. When he wrote, he felt calm and centered, and removed from himself in a good way, but when he thought about his life in the big picture sense, he always ended up feeling stressed and overwhelmed, about how badly he had messed things up in the past and about what he should do with himself now and in the future. It still didn't seem real that he was a high school drop-out. The label embarrassed him, even if he had earned it all on his own.

He thought about his social life, or lack thereof. He had broken ties with the one friend he had had left from his high school in New York when he had moved out of his last apartment without notice. Anton had been understandably pissed after vouching for Jess with his other two roommates to get him in to begin with. But, Jess had felt that he needed to jump on the opportunity for this studio and the chance to live alone, so he had done what was best for himself and left his friend in the lurch. He had never bothered to apologize to Anton or try to smooth things over. It was just one more broken bridge in his life. Anton became just another person that he used to know. Jess thought about how few meaningful connections he had in the world. Luke. Liz, when she felt like being a mother. When he had run off to California, he had thought he would be able to develop a relationship with his father, but that hadn't gone as planned and Jimmy didn't make the list. He had Dean. For now. But, he realized that Dean would never be able to support Clara in the city. Everything was too expensive there. If Dean got custody of his sister, he would need to return to Stars Hollow. He wondered if their new friendship would survive the distance. There had been a time when he couldn't have pictured not being in contact with Rory, but they hadn't survived his leaving for California. Granted, he hadn't said goodbye or actually told her he was leaving…. He sighed at his own stupidity. No wonder he didn't have friends. He was selfish. He often acted impetuously and didn't take other people's feeling into consideration to the extent that he should. He knew that. He had always been a shitty friend because of it. Then a shitty boyfriend. To Shane and then to Rory. He didn't think he had messed anything up with Dean yet. He thought back to a drunk Dean up in his face, telling him he didn't have friends and never went out. Jess lived like a hermit at nineteen. It wasn't normal. He needed to get out more and have some semblance of a real life beyond his books and writing. Dean had been a jerk that night, but he had been right about that.

Jess' mind drifted to Dean then and the appointment he was currently at with one of Nicole's colleagues. Luke had called Monday to tell Dean that he had set up an appointment with him for Thursday afternoon. Jess had offered to go with him since it was his day off this week, but Dean had said he wanted to go alone. That he felt like he would come across as more adult if he showed up on his own instead of dragging his best friend along with him for moral support. It had given Jess pause to hear that. It made sense logically. If Dean had a better friend than him out there, he probably would have sought out help from them instead of living on the street. But, it seemed odd to Jess that Dean didn't have someone else he was closer to. He had always seemed friendly and popular in high school. Jess had never been anyone's best friend before. He wouldn't take the title lightly. He just hoped it wasn't situational. He liked Dean and he really wanted to know him for a long time. He wanted to be able to add him to his short list of people in his life, under Luke, but probably above Liz.

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Jess looked up as Dean entered the apartment a couple of hours later, a big smile on his face. "Hey, how did it go?"

"It went well. I think it went really well." Dean pulled off his jacket and hung it up. He poured himself a glass of water and leaned against the counter. "I mean, they didn't laugh me out of the place or anything. So that's something, I guess." Dean laughed.

"It sure is." Jess agreed. "What did they say?"

"Well, I met with Nicole, who, you're right, is really pretty. Between her and Lorelai, Luke seems to do pretty well for himself, huh?"

Jess smiled. "I'll give you that Nicole is pretty and that Luke was most definitely dating up when he was with her, but that's all I can agree with in that sentence."

Dean laughed. "Anyway, the other lawyer, Raina, that Luke had mentioned. She's really important. I think she's like in charge of the whole family law department. She's a partner and everything. I used to see these younger lawyers, like the ones who just got out of law school, at my uncle's firm. They'd be working round the clock, just totally crazy stressed out. I pictured Nicole giving my case to one of them. Not a partner. But, I got the impression that they know my uncle and don't like him and that maybe it's a little personal for them, too. Which is cool, right? I mean, whatever got them motivated to take my case can only help me."

Jess nodded, head tilted to one side, thinking this over. "I don't think it can hurt. Especially if it means they're bringing out the big guns."

"Oh, get this. They even gave me a job!"

"Huh. Dean Forrester, Esquire. Has a nice ring to it. You should get business cards printed."

Dean laughed. "It's in their mailroom. When I said I had worked in the mailroom at my uncle's firm and that I only had a part-time job right now, they said they had an opening. It's full-time, with benefits and I'll start at two dollars more an hour than I made at my uncle's place."

Jess' face registered surprise. "Seriously? That's amazing, Dean. Congratulations."

"Thanks. I start in two weeks because I told them I needed to give notice at the convenience store."

"That was very considerate of you." Jess had a fleeting thought that if he were in Dean's shoes, he would have jumped on the offer, telling them he could start tomorrow and blowing off the remaining hours he was scheduled to work at the convenience store. But, Dean wasn't like that. Jess wondered if Dean would still want to be friends once he got to know Jess better and saw what a jerk he could be when he wasn't busy taking in homeless people.

Dean shrugged. "I always figure what goes around comes around, right? And, they said this job would make me look better when I petition for custody of Clara. I told them I wouldn't be able to keep it for long because I'd probably have to go back to Stars Hollow, or someplace even cheaper, in order to afford an apartment for me and Clara, but they said that's ok. That it would still make me a stronger candidate for custody. Like, it would show I was capable of holding down a full-time job and that I would have reputable references when I applied to jobs somewhere else. And Nicole said Luke had vouched for my character. I really need to thank him for putting me in touch with her. Just being able to talk to Nicole and Raina today and knowing that the idea of me getting custody of Clara isn't completely rediculous makes me feel so much better."

"That's great, Dean. I'm really glad it went so well." Jess stretched and got to his feet. "How about I take us out to dinner to celebrate?"

Dean smiled. "You don't have to do that, Jess. There's stuff I can make here for dinner."

"I know. I just really feel like getting out of the apartment tonight. And I want you to come with me."

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Once they were settled in at a table at the pizza place down the street from Jess' apartment waiting for their order number to be called, Jess asked the question he was most concerned about. "So, did they give you an idea of how long the whole process would take?"

Dean dug through his jacket pocket as he nodded. "Yeah, they said it will take a few months, at least. That there are things I need to do to be able to show a judge that I can take care of Clara." He pulled a folded piece of paper from his pocket and waved it at Jess. "I even took notes." Dean unfolded the paper and looked at it. "So, they set up an appointment for me with a social worker at Child Protective Services. They said my petition would be more 'compelling,' that was their word, if we have social services on our side. I have a meeting with her next week, but Nicole said she's already talked to her and given her a heads up about my situation. I need to get letters of reference from adults who know me and Clara and who can vouch for me being responsible enough to take care of her. Nicole said to look for upstanding members of the community. She suggested Luke. Do you think he'd do it?"

Jess nodded, convinced Luke would be happy to help Dean any way he could. "Yeah, I think he'll do it."

Dean's expression turned uncomfortable. "And you think it's ok to ask him? I mean, he's already done so much for me? Do you think it's too much?"

"I think it's ok to ask him. I can't guarantee it will be Shakespeare. Or that it will even make sense. But, I know it will make Luke happy to write it, and I know he'll be very generous with his praise."

Dean smiled. "Yeah, ok. I think he'd do a good job. I was thinking of asking Lorelai, too. And Mrs. Fowler, the mother of Clara's best friend, Sabrina, in Stars Hollow. She always liked me and thought I was a good big brother. And maybe Taylor."

Jess snorted. "Oh, wait, you're serious? You really trust him to do that?"

Dean laughed. "Taylor's a good guy. You just didn't know him."

"I knew enough. That guy was out to get me the second I set foot in that town."

"Oh, c'mon! The second you set foot in town, or the second you stole the bridge fund money or set up a fake murder scene in front of his store?"

"That hurts, Dean. Whose side are you on here?"

Dean laughed. "Hey, I'm the one who had to spend the day scrubbing that chalk outline off the cement!"

Jess smiled. "I remember. That was the best part."

"Really?" Dean smirked. "I would have thought the best part was impressing Rory with your hooliganism."

"Hooliganism? Ok, grandpa. I guess you and Taylor really do have a lot in common. I can see why you're such good buddies."

"Anyway, I worked for Taylor and he always liked me. And he's the town selectman and owns his own business and a few apartment buildings in town. That's about as upstanding a member of the community as Stars Hollow has, right?"

"If you say so." Jess reflected on the fact that Dean had only been in Stars Hollow a year longer than he had, and if he had to come up with character references, he would only have Luke, maybe Caesar, and possibly Kirk. Kirk had always liked him, but his letter would likely be gibberish. "What else do you have to do?"

"I need to fill out a bunch of forms, like for background checks, and stuff like that. And, I need to get fingerprinted. But, I guess I do all that stuff with the social worker next week. I need to write a letter to Child Protective Services on why I want custody of Clara and why I think she would be better off with me than with my aunt and uncle. Clara will need to write one, too, about why she wants to live with me. They said to include the details about how my uncle threw me out, and gave away my stuff, and about Clara hearing my uncle hit my aunt, and that it's really important for that to get into the social worker's court report and get on the record. I need to prove I can take care of Clara financially, even before I get the money from my parents'. Raina said if I get custody, there may be ways around the stipulation in their will that I don't get any of the money until I'm twenty-one, but that I need to prove I can provide for Clara without it, in case I don't get it early. She said right now, it's important for me to stay in the city and maintain regular contact with Clara, which I planned to do anyway. She said since Stars Hollow is so far away from where Clara is, that I don't need to worry about actually getting an apartment there until I get custody because that shows that being close to Clara is my top priority. She said in cases like this, the judge can award me custody and then give me a month to get things in order with a job and an apartment. Raina said the most important things I can do right now are to have a full-time job, which I have now thanks to her and Nicole, and to save money to show that I have the ability to pay first, late and security on an apartment and buy furniture and stuff when I get custody." Dean's expression turned nervous then. "But, I'll still give you money for rent and bills and stuff, of course, once I get my first paycheck. I'll just try to save money on top of that. I know I owe you my first few checks for everything you've done for me. I don't want you to think I don't know that."

"Don't worry about paying me. We can split the groceries if you want, but I'd be paying rent and all the other bills anyway. You aren't costing me anything there. And, besides, this is more important."

Dean was shaking his head. "No, Jess, I didn't mean-"

"This is more important, Dean. Seriously. You don't owe me anything."

"That's not right, Jess. I do owe you. You need to let me pay you back."

Jess sighed. "Fine, but you don't need to do it right away. I think you should worry about saving for this first. After you have Clara and you're back in Stars Hollow, bagging groceries for Taylor again" Jess smirked. "you can start worrying about paying me back. Ok?"

"Ok, Jess. Thank you. Really."

Jess shrugged. "It's in my own self-interest. Do you have any idea of the earful I'd get from Luke if he knew I was taking your money for bills when you need it to help you get custody of your sister?"

Jess was feeling uncomfortable under Dean's carefully scrutinizing gaze. "I really hate it when you do that, Jess."

Jess tried to shake off the comment. "I don't know what you're talking about."

"Yes, you do. When I thank you for something, and you act like you didn't do anything worth being thanked for." Dean watched Jess avert his eyes, glancing toward the front of the pizzeria as though checking if their order was up. "Like, the time I thanked you for letting me spend the day with you and Luke when he came to visit and you said I was the one doing you a favor because I diverted some of Luke's mother-henning away from you."

Jess was trying to be casual as he kept his gaze away from Dean. He wasn't sure why Dean's thanks made him so uncomfortable. He thought diminishing the need for thanks would make things easier on both of them. "You did. And I don't think I've ever used the term mother-henning in my life, though it definitely suits Luke."

"It makes me feel like crap when you do that, Jess. Like whatever I'm grateful for is so insignificant to you that you don't think I should bother thanking you. Even when it's something that feels really big to me. I feel like your attitude about it demeans both of us."

Jess looked back at Dean now, making eye contact again. Not knowing how to take that. Not being accustomed to that level of sincerity and open honesty. Part of him feeling attacked and wanting to get defensive. The other part knowing that would just be a coping mechanism to distract from the earnestness of what Dean had just told him. Jess knew he should take Dean's comment on board and process it and try to change the behavior that was making Dean feel bad. That's what you did when you cared about someone. He knew that. He needed to meet Dean's honesty with some of his own.

"I'm sorry. I'll work on that."

Dean smiled sincerely at Jess, and Jess was relieved, not that attack was over, but that it hadn't been an attack at all. "Thanks, Jess. I appreciate that."

Jess smirked back. "You're very welcome, Dean."

Their order was called. Dean clapped Jess on the arm as he got up to collect their food. "Aw, see that, Jess? You're learning already!"

Jess watched him go with a small smile on his face.


	14. Chapter 14 - A Plan in Motion

**Chapter 14 Notes:** Dean and Jess work toward their goals. This chapter includes a minor deviation from the show in regards to Jess' car. Thank you to everyone who is still reading and to everyone who has left me reviews on this story. They keep me going! :)

 **Disclaimer:** I own nothing except my own obsession with Gilmore Girls.

 **Trigger Warning:** Homelessness. Mentions of 'off camera' domestic violence.

Dean pushed his way through the revolving door and exited the lobby of the sky scraper that housed the law firm. It wasn't quite spring, but Dean could tell it was just around the corner. He was still wearing his winter jacket, but without a hat, scarf or gloves. Pretty soon his jacket would be too much, and he would need something lighter. Even though he was making decent money now, the best he had ever made in his life, working in the mailroom, he hated the idea of taking anything out of savings to buy clothes or anything else for himself. He was proud of how much he had saved and very careful about how he spent it. Taking Clara to a movie or a museum on Sundays? Money well spent. Buying groceries or bringing home the occasional cheap takeout dinner for himself and Jess? Totally acceptable. Buying himself a new jacket? Not so much. Maybe he could hit up the Goodwill and see if he could get something really cheap. As it was, he was still making do with what Luke had bought him with very little in the way of wardrobe upgrades. He had invested in a cheap second dress shirt after Nicole and Raina had hired him to work in their mailroom. He wore the chinos from his shopping trip with Luke to work every day, along with one of his two dress shirts. He felt like he could get two or three days out of each shirt as long as he wore a fresh undershirt every day. Then every Saturday, he washed all of it and started over on Monday.

Even though he was still vigilantly watching his money and was not yet in possession of what most people would consider a complete wardrobe, the penny-pinching and sacrifice felt good now. Instead of feeling sorry for himself, he felt empowered. Having his own income again felt amazing. He knew he had lucked into this job. That the offer had likely come from a mix of Nicole and Raina feeling sorry for him and wanting him to have what he needed so that they could beat his uncle in court. But, Dean didn't mind. He wasn't stupid enough to look a gift horse in the mouth. No sir. He may have gotten this job by chance and he may not be able to keep it after he got custody of Clara, but he was determined to make the most of it and have as positive an experience as possible. He worked hard every day, sorting mail, delivering it throughout the office, volunteering to run errands or clean up or do anything else that his co-workers seemed less than enthused about, and greeting everyone he ran across at the office with the cheerful smile of someone grateful to be working and saving money toward his goal. He heard some of the other guys in the mailroom and even some of the attorneys complaining about their jobs or the hours they worked, and while Dean realized he was new to the labor force in general and may someday become that jaded himself, he knew it would be a long time until he would complain about any job he worked. He had only to remember the long, lonely and frightening nights he had spent on a cot at St. Sebastian's or the days of trying to look inconspicuous as he huddled in the library for warmth to feel a swell of gratitude at being able to work and take care of himself. Even though Jess had warned Dean away from ever saying it out loud at work, Dean loved his job. To top it off, they had television screens mounted in the elevators and every Friday, one of the attorneys brought in a box of fancy donuts for the guys in the mailroom. Dean smiled remembering the maple donut he had had that morning, with actual bits of bacon in the frosting. They had everything in this city.

Dean entered the subway station and after several stops and one line transfer, he exited in the neighborhood near Jess' apartment and headed into the cheapest nearby market. And after spending one Saturday morning going into all the markets in close proximity to the apartment with a pen and notebook and conducting some serious comparison shopping research, Dean felt confident that he knew which was the cheapest as opposed to just being the most convenient. Every dollar counted. Dean had recently checked out a new cookbook from the library, one whose cover advertised that it contained fifty cheap and easy stove top recipes. He had spent a few hours the previous night, paging through it, and copying down the recipes for things that looked cheap and easy enough for him. He needed to pick up the ingredients for a pumpkin chili he wanted to make. Dean smiled to himself as he picked up a shopping basket and headed down the first aisle.

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Jess was sitting at the table in his apartment, laptop open in front of him. He had to admit that Luke had been right about them needing a table. He had gotten a lot of writing done sitting at this thing. He felt more productive, that he could focus on his writing for longer stretches of time when he was sitting at the table as opposed to curling up with his laptop on his mattress. Not today, though. Nothing seemed to be getting done today. Not that it was the table's fault. It was all Jess. He sat in front of his laptop, staring at the blue 'Submit' button in front of him, but too immobilized by fear to actually click on it.

He knew his story was done and as close to publishable as he could get it on his own. He had settled for describing it as a novella because of its length. After his final go at editing it a few weeks ago, he had set himself the goal of researching potential publishing houses to send it to. And he had. He had looked at some of the large companies that published the majority of what was read in this country. He had looked at newer, smaller companies that were just starting up and seemed to focus on niche markets. He had scoured the internet for resources on how to best approach this and where to send his manuscript. He felt ridiculous even calling it a manuscript. He had no idea if it was anywhere near worthy of being published. He had decided to start with a small, independent publishing house located in Philadelphia. Mostly because of the young and edgy feel of their website, where they claimed they were proud to publish work that you wouldn't find put out by Penguin or Random House. He had sought out some of the novels the company had already published and had liked what he had read. He had also had a small freak-out about whether his writing was of the same caliber. If nothing else, the company was only a little over a year old. Jess hoped this meant that they couldn't be too picky just yet, and that maybe they had time to work with aspiring authors on getting their novels up to publishable standards. His finger hovered over the keyboard.

He wished he had someone else who could read it and weigh in on its merits and failings before he sent it off. Luke would read it for him if he asked him to. He knew Luke would be more than happy to do that even though he had never actually seen Luke read anything else. He also knew that Luke's critique would be based more on his love for Jess than the actual quality of his writing, and that Luke would lavish praise on him whether his writing deserved it or not, making Luke a better parent than literary critic in Jess' opinion. He knew Dean would be willing to read it, too, and again be happy to do so, but since he and Dean didn't seem to agree on anything else they read, he worried that Dean might honestly dislike it, and he didn't want to put the guy in an awkward spot of having to tell him that. He couldn't help thinking he would like to have Rory's thoughts on his story, no matter how unrealistic that idea was. He sighed. He needed to be a grown up and just send it out already. He had done harder things on his own in his life than hitting one little 'Submit' button. He could do this.

Jess was startled out of his thoughts by the sound of a key in the door. He quickly hit the X in the corner of the screen to close out of the website and slammed his laptop shut without bothering to turn it off. He knew he was acting like a spaz. Dean saw him on his laptop all the time. It's not like he would have known what Jess had been up to and thought he was a coward for not being able to go through with it.

"Hey, Jess!" Dean entered, cheerful as usual, loaded down with two grocery bags. His expression turned quizzical as he looked at Jess, who realized too late that he was leaning forward on the table, his forearms crossed protectively over the lid of his closed laptop, painting the overall suspicious picture of a kid who had been caught with his hand in the cookie jar. "What's with you? Did I interrupt your porn time or something?" Dean laughed at his own joke.

"Haha." Jess said, recovering from his surprise. "No, but now that you mention it, I've been meaning to talk to you about all the gay-midget-bondage-porn you've been looking at on the computer. Now I'm not judging. To each his own and all that. But, if you wouldn't mind going forward, could you please close out of the website when you're done getting your rocks off so that I don't get an unwanted surprise the next time I start it up? It's only good roommate etiquette after all."

"You're ridiculous." Dean laughed and set the shopping bags down on the kitchen floor. "I picked up some groceries." Jess watched in amusement as Dean pulled a bag of cereal out of one of the shopping bags. Dean had learned it was cheaper to buy it in bags than in boxes, and for some reason that cracked Jess up.

"I see that. How much was it?" Jess stood up and walked over to the little plastic bin that he used as a bureau, grabbing his wallet off the top.

Dean looked back over his shoulder toward Jess as he placed a can of beans in the cabinet. "Oh, no, Jess. That's not what I meant. Don't worry about it. I got it."

Jess removed the sole contents of his wallet, a ten and a twenty, and walked over to Dean. "Here you go." He held the money out toward Dean.

Dean turned to face him now, can of pumpkin in one hand, making no move to take the money. "Really, Jess. I'm good. I want to get it this time."

Jess gave Dean his sternest look, the one he usually reserved for Luke when the man was going overboard with his nagging. "Dean, our agreement when you started working was that we would split the groceries, not that you'd buy them all."

"We can split it next time. We'll go together."

"You keep saying that, but you also keep going to the grocery store without me and then telling me that we can split it next time. So, you can see why you have no credibility at this point, right?"

Dean huffed out a laugh. "I can see what you're saying, yes. But, seriously, Jess. You're paying the rent and the bills. I want to get the groceries. I know it's nowhere near even, but it makes me feel like I'm at least paying a little bit of my own way and still helping you out. I want you to feel like you're getting some benefit from me being here, too." Dean smiled. "Other than the pleasure of my company, obviously."

"Dean-" Jess got ready to start scolding in earnest as he lowered the hand holding the money to his side.

"I'm serious, Jess." Dean said, smile gone, replaced by a stern look of his own. "I need to feel like I'm contributing here. I'm keeping a list of the rent and bills and stuff. And once Clara and I are settled, I'll start paying you back for half, like we talked about. I have a running list of what I owe Luke, too, for all the stuff he bought me. And I plan to make good on that, too, down the road. But, I need to feel like I'm doing something right now. Ok? I'm still saving money. I'm doing all right, I promise. You letting me pay for groceries isn't going to make it so I can't get custody of Clara. I swear."

Jess sighed. "I get what you're saying." Jess slid his money back into his wallet as he thought about not graduating high school because it had felt so important to prove his independence by working as many hours at Walmart as he could get, the goal of taking care of himself looming large in his mind. He knew now that it hadn't been the right path to independence for him then, but, maybe this was the right path for Dean now. Maybe he felt the need to contribute to their little household as strongly as Jess had felt the need to earn his own money, away from Luke and the diner. Maybe the feeling of paying his own way was more important to his survival than the money spent to earn it. And if Dean said paying for groceries wasn't going to impact his chances of getting custody of his sister, Jess felt like he had to believe him. "I would probably feel the same way in your shoes."

"You would, Jess. Trust me."

Jess thought for a minute. He knew the cost of monthly groceries was much lower than what he paid for rent and utilities, but it wasn't insubstantial either. Now that Dean was working and in better spirits, the guy could really eat. "How about this? I won't give you money when you buy groceries? But, I'll buy them sometimes, too, and you won't give me money then."

"Jess, that defeats the whole purpose-"

Jess turned and walked away to put his wallet back on top of the storage container. "Maybe I like going grocery shopping sometimes. Why would you want to take that joy away from me?"

"Oh, c'mon." Dean laughed. "You do not!"

"I do too. It's peaceful there…" Jess trailed off as he walked back over to the kitchen area and took in Dean's suspicious expression. "And, you never buy the peanut butter cookies I like."

Dean smiled as he put a bag of apples in the fridge. "Are you serious? Those things will rot your teeth!"

"Says the guy whose only luggage when he moved in was a bag full of gummy bears and Pop-tarts."

Dean was laughing now. "You know Lorelai sent that stuff! And if I remember correctly, you ate more of it than I did. I haven't been buying sugary stuff since we're both trying to save money and that kind of stuff not only doesn't add anything to your health, but sugar can also interfere with your body's ability to absorb and use the vitamins and minerals you take in from other food. Did you know that? It's insane how bad it is for you! I just learned that in the cookbook I'm reading. And I don't know about you, but I don't have dental insurance."

"Yes, Luke." Jess smirked, as he started to poke through the second bag. "Whatever you say, Luke." He grabbed a container of milk and took the two steps over to the fridge. "Let's just live off spinach and tree bark, Luke."

Dean shook his head, smile on his face. "You're such an ass…."

"But seriously." Jess went on, pulling a head of garlic and an onion from the grocery bag and setting them aside on the counter. "You should keep a list of what you spend on groceries, too, and deduct half of what you spend from what you owe me for your half of rent and bills. Sound fair?"

Dean watched his friend crouch down to pull the next items out of the grocery bag, wanting to be stubborn and push back, but aware that Jess was only looking out for his best interests. Dean felt a warm rush of appreciation that after everyone he had lost he still had someone in his life who was. "Ok, Jess. If that makes you feel better. I'll keep track of that, too." Dean figured he could always fudge his numbers later so that he could pay Jess whatever he felt was appropriate.

Jess nodded. "Ok, good. See, now it's fair and everybody's happy."

Dean smiled. "But, you're on your own for your peanut butter cookies. I can't in good conscience support your dirty little habit."

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"All right." Dean turned to face Clara and Jess. "I'm going to run to the bathroom before we get back on the train. Clara, do you need to go? It's a long train ride back to Aunt Gretchen's." It was Sunday afternoon and they were about to exit the American Museum of Natural History. Dean had invited Jess to join him and his sister on their weekly outing, and since Jess had the day off and no plans apart from finishing up the book he was reading and since he was trying to get better about actually leaving the apartment once in a while, he had agreed. A few hours later, he had been reminded of both how impressive and how crowded the natural history museum was. Liz had briefly dated a grammar school science teacher when Jess had been little, maybe six or seven. He had taken Jess to a children's program at the museum where a group of kids and parents got to sleep overnight in the museum and get an up-close and personal tour of everything after the crowds had gone. He could still remember being allowed to spend as much time as he wanted staring at the dinosaur skeletons in awe. Jess couldn't remember the teacher's name, but he remembered how much he had appreciated not being rushed. The few times Liz had bothered to take him to museums or zoos or aquariums because she felt like she should, she had always rushed him along to get the experience over and done with. The museum sleepover was one of the coolest things Jess had gotten to do in his childhood.

Clara rolled her eyes. "I'm twelve, Dean. Not six. You don't need to ask me if I need to go to the bathroom."

Dean put his hands up, palms facing out. "Sorry. You're right. Wasn't thinking." He smiled as he turned his attention to his roommate. "What about you, Jess? Do you need to go to the bathroom?" Clara giggled.

Jess cocked an eye brow and feigned serious concentration as he thought over Dean's question. "Nah, I'm good, too. Thanks for checking, though." Clara giggled again.

"All right, you two. I'll be right back. Meet you at that bench over there?" Dean pointed to a long bench near the exit door.

"Ok." Clara said as she started to head towards the bench.

"And, Clara?" The girl turned back toward her brother. "You're in charge while I'm gone. Keep an eye on Jess and make sure he doesn't wander off." Dean nodded seriously at his sister, then broke into a grin and walked away.

Clara rolled her eyes with a smile and sat down on the bench with Jess. "Dean makes really lame jokes. My dad did, too. I think it runs in our family, for boys at least."

Jess thought about the things Luke often passed off as wit. "I'm pretty sure it runs in every family."

Clara giggled. "But, Dean's really great. My parents were, too."

Jess nodded seriously, hoping the topic would quickly shift from Clara's deceased parents. He barely knew what to say when Dean spoke about their parents. He felt in no way qualified to talk to a twelve-year old about that kind of loss, but he knew he needed to listen if that's what she chose to talk about. "That's pretty special. Being really great is definitely not something that runs in every family."

Clara smiled at that, and Jess gave himself a mental pat on the back for not making things worse. "Did Dean tell you that he's trying to get custody of me?"

Jess nodded. "He did."

"I hope he gets it. I hate being separated from him. Do you think he'll get it?" The serious and concerned look on Clara's face was tugging at something in Jess' chest. He wanted to tell her that everything would work out, but he didn't want to say more than he really knew to be true.

"I know he has two very good attorneys working with him. I think he has a good shot."

Clara nodded, taking that in. "If he gets custody, we're going to move back to Stars Hollow. But, in an apartment, not our old house. The house belonged to our grandmother and now it's half ours and half our uncle's, but we don't get our half until Dean is twenty-one."

Jess had heard all this before from Dean, but still nodded respectfully as he listened.

"I really miss Stars Hollow. My school and all my friends. Don't you miss it?"

Jess considered her question. What came to mind was a bought of food poisoning he had had before Dean had moved in. He had attributed it to eating expired yogurt, not realizing it had gone bad. He remembered being up all night by himself, dragging himself to the toilet to vomit or have diarrhea, holding a damp washcloth to his head and shaking with chills, feeling sorry for himself and longing for Luke. "Sometimes I do."

"Are you going to move back when we move? Maybe we could all get an apartment together." Clara gave Jess the same shy, hopeful smile he was accustomed to seeing on Dean. The one that made him agree to stuff he didn't really want to do. For a split second he considered saying yes.

"I don't think I'll ever move back there, but I go back sometimes to visit Luke. And, I bet I'll go back more often once you and Dean are there, too."

Clara frowned.

"What's the matter?" Jess prodded gently. "Are you worried about something?"

"What if Dean changes his mind? And decides he doesn't want me to move in with him? What if he likes it better living with you, where he doesn't have to take care of a kid?"

Jess was shaking his head before Clara had even finished her questions. "That's not going to happen, Clara. Ok. Listen to me. Dean loves you and wants to be with you more than he wants anything else. He's not going to change his mind about that. Trust me, ok?"

Clara's eyes were filling with tears. Christ, how did this day go to shit so quickly while Dean was in the bathroom?

"I know he's scared." She whispered.

Jess wasn't sure how to respond. Of course, Dean was scared. Taking on the responsibility of being a child's legal guardian, even a good kid like Clara, seemed scary as hell to Jess. He had a flash of memory of Luke welcoming the nephew he had barely recognized as he got off the bus on his first day in Stars Hollow. Luke had to have been scared out of his mind with what he was taking on. "Why do you think he's scared?"

Clara wiped her eyes with the back of her hand. Jess wished he had a tissue to offer her. "I could tell. He acted like he wasn't when he told me he was going to try to get custody, but I could tell he was."

Jess didn't know how to respond, so he asked another question. "How could you tell?"

"Because it felt like the time in Chicago before we moved when Dean was supposed to be watching me while my parents were out of town. He wasn't supposed to have friends over, but he did, and they broke something of my dad's and Dean was scared about telling my parents. He tried to convince me he wasn't scared to tell them, but he was."

Jess reflected on this. "I would be scared in that situation, too. Did he tell your parents the truth even though he was scared?" Jess was putting his faith in sixteen-year old Dean's morality, knowing he wouldn't be able to make his point if Clara said no.

The girl sniffed and nodded. "Yeah, he told them what happened as soon as they got home."

"Well, there you go." Jess gave her a warm smile, happy with the conclusion of this conversation.

"What do you mean?" Her brow was furrowed.

"He was scared, but he did it anyway because it was the right thing to do. He'll do the same thing now, even if he is scared. Dean's a good guy like that."

Clara was smiling at Jess as Dean walked up to their bench. "You guys stay out of trouble while I was gone?"

"Jeez, Dean, what did you fall in or something?" Jess snapped, and Clara giggled.

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A few days later Jess got a call as he and Dean were finishing up dinner. He got up to check the screen and saw Clara's name lighting up as the phone buzzed. He hit accept and handed the phone to Dean. "It's your sister." He started to clear their plates to give Dean some semblance of privacy for his call in the tiny apartment. He couldn't help overhearing anyway.

"Hey Clara, what's up?...Oh, no. I'm sorry to hear that. How did it happen?...Is she ok?...Ok. Good. I hope you're helping her out while she's hurt…..Oh, right, Sabrina's party…I know you're really looking forward to it…I know she's your best friend…Yes, I'll take you…." Jess watched Dean break into a grin. "What? No way! That is such a coincidence because you're the best _sister_ in the world!…It's no problem. I know how much this means to you….and you ran this by Aunt Gretchen, right?….Ok, we're on.…..What time is the party?... Ok. I'll look up the bus schedule and call you back tomorrow after I get out of work, but we're definitely doing it, ok? Don't worry about anything. You will be at that party….." Jess saw Dean shoot a furtive glace his way. "I don't know. Maybe. I'll ask him….ok, yes, you better finish that homework….ok…I love you, too.….Bye, Clara."

Jess pretended to wash a dish as he waited for Dean to end his call. "Everything ok?"

Dean pushed a stray lock of hair behind his ears and looked over at Jess from where he still sat at the table. "I'm not sure. My aunt has a broken wrist."

Jess started hesitantly. "And do you think your uncle…."

Dean shrugged. "I don't know. It was my first thought, definitely. Clara spent the night at a friend's house last night and when she got home after school today, Aunt Gretchen had a cast on her wrist. She told Clara that she fell while she was out running yesterday, put out a hand to catch herself and broke it that way."

"But, you don't believe that?" Jess asked, abandoning all pretense of washing dishes and turning around at the counter to face Dean.

"I don't know. Aunt Gretchen is a pretty serious runner. She goes out almost every day. It's certainly something that could have happened. I don't know what I can do about it, either way. Part of me is at least grateful that if it happened while they were fighting, that they at least waited for Clara to be out of the house."

"What does Clara think? She must be worried if she called to tell you about it."

"Oh, well, she actually called because this weekend is her best friend Sabrina's slumber party for her thirteenth birthday, back in Stars Hollow."

"Oh, yeah." Jess nodded in recognition. "I remember her saying something about that at lunch on Sunday. She seemed really excited for it."

"Yeah, she is. And tonight, she was flipping out because Aunt Gretchen had promised to drive her there. She was going to stay in a hotel and drive her back the next day. But, she can't now because of her wrist, and she doesn't want Clara to go by herself. I don't really want her to either. So, I said I'd take her."

"Oh."

"Do you want to come with us? You could visit Luke."

"Maybe." Jess hadn't planned on a trip to Stars Hollow anytime soon, but he thought it might be fun to go with Dean. And Luke was always asking him to come visit. "You going Saturday to Sunday?"

"Yeah, the sleepover is on Saturday night."

"I'm scheduled to work Saturday, but I'll ask around tomorrow and see if I can get someone to switch with me."

"Cool. And you think Luke will let me crash on your couch or something, right? Do you think that's ok for me to ask?"

Jess rolled his eyes and spoke slowly as if stating the very obvious to someone very slow. "Yes, Dean. We'll stay with Luke. If I can't switch my schedule and go with you, Luke will still let you stay with him anyway. I think he'd be pretty offended if you went to Stars Hollow and rented a room for the night instead of staying with him. I'll call him tomorrow and give him a heads up."

Dean huffed out a breath. "Ok, thanks. I hope you can come, too."

"Me too. I'll see what I can do."

"And it's probably good for me to go back anyway. Even if it's too early to rent an apartment, I feel like I should start looking around and getting an idea of how much they cost, and maybe start talking to Taylor about whether he has any job openings coming up, or any openings in the apartments he owns. Stuff like that." Dean sat back in his chair and ran a hand through his hair. "Shit! You know what I just realized?"

"That Taylor's a jerk and he really shouldn't play such a large role in planning your future?"

"No." Dean frowned at Jess. "That I'm going to need a car when I move to Stars Hollow. We're probably going to end up out where the cheaper apartments are, like out by the Walmart, nowhere near the center of town. I'm going to need a car to get around if I live out there and work for Taylor in town. And I'll need a car to take Clara places, like to Sabrina's house or to pick her up from tennis practice. I can't believe I didn't think of this sooner." The money Dean was so proud of saving was starting to feel less adequate as he thought about a car and the associated expenses like insurance and maintenance and gas. He couldn't believe this was only dawning on him now. His list of expenses looming just around the corner kept growing. He had had a mini-panic when he had given notice at the convenience store and realized he would need his own phone and phone plan and maybe even one for Clara so he would always know where she was. He hadn't thought about the phone until he had been saying goodbye to Angela on his last day and almost asked for her number to stay in touch. He had really liked her and she had mentioned that he should come out with her and her friends one time when he had said he was new to town and didn't know anyone except his roommate. He had caught himself before asking when it hit him that she might ask for his as well and the idea of telling her that he didn't have a phone and that she would need to call him on Jess' had seemed too embarrassing to contend with. He had gone home and added phone expenses to his projected budget that night. Now, he needed to add a car, too, and a car was huge.

"You can use mine if you want."

"You have a car? I thought your car was stolen. I remember hearing Babette and Miss Patty talking about it. Babette thought it served you right for stealing her lawn gnome. I had never seen her so mad before."

Jess snorted. "Yeah, she was never my biggest fan. Even after I returned that stupid looking thing."

"So, it wasn't stolen?"

"Only temporarily. Pierpont the gnome was returned unharmed to Babette's yard the very same day of his disappearance."

"I meant your car, not the gnome."

"Oh, that was only stolen temporarily, too. And only by Luke. He put it in storage and let me think it was stolen so that I couldn't drive out to Walmart for work. He thought being carless would make me go to school instead. He was worried that I wasn't going to graduate because I was skipping too much school to work." Jess shrugged. "And I guess he was right in the end about me skipping too much. Not that stealing the car helped anything. But, yeah, when I learned that he had it I left it with him. Having a car in the city would have been way too expensive and too much hassle. If it's still running, you're welcome to use it."

Dean was giving Jess an incredulous look. "If he wanted you to stop skipping school to work at Walmart, why didn't he just ground you and take away your car keys? Wouldn't that have been easier, and you know, more normal?" Dean smirked. "Or does your whole family just have a penchant for creating fake crime scenes?"

Jess laughed. "Taking away my keys does sound more reasonable now, but I don't think it would have occurred to either of us then for him to just ground me like that. He nagged me about shit all the time when I lived with him, told me I had to finish school, made me return stuff I stole. Stuff like that. But, he never once actually punished me for doing something he told me not to. I don't know. I think he always tried to kind of treat me like an adult. Maybe it didn't work as well as he'd planned since I did end up getting kicked out of school." Jess reflected on whether Luke hadn't just grounded him and taken his keys like most parents would have because he didn't trust Jess to not steal his keys back, or even to hand them over to begin with. He felt the same twinge of guilt he always got when he thought about what a little shit he had been to Luke when he had lived with him. "Anyway, when I call Luke tomorrow, I'll ask about the car. I know he checks on it and starts it every once in a while so I'm guessing he would have mentioned it if it ever didn't start for him."

"That would be great. Thanks, Jess. I really appreciate that."

Jess was about to say it was nothing, but then his memory flashed back to their conversation at the pizza place a few weeks ago and a small smile formed on his face as he remembered what he had promised to work on just in time. "You're welcome, Dean. I'm happy to do it."

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Later that night, Jess was lying on his mattress in the dark apartment, wide awake despite his best efforts to fall asleep, his mind still stuck on his conversation with Clara at the museum last weekend. He looked over at Dean, already sleeping soundly on his roll up mattress, and thought about how scared he had to be. About taking on the responsibility of caring for another human being. And a small and sensitive one, at that. Jess couldn't imagine doing that at their age, maybe ever. Most days he felt like he could barely take care of himself. Even though Dean didn't talk about his fears, Jess knew he had to have them. This was a big deal. By far the biggest thing either of them had ever done. Taking care of a child may be the biggest thing anyone could possibly do. Dean had to be scared, Jess reasoned. That he wouldn't be good enough. That he would mess up and make things worse. He was too smart not to be. Only a fool would have no fear about something as huge as this.

Jess churned that thought over in mind. Dean had to be scared, but he was doing it anyway. Luke had to have been scared when he had taken in his teenaged punk of a nephew, but he had done it anyway. Jess booted up his computer in the dark. He was scared, but he was going to hit 'Submit' anyway.


	15. Chapter 15 - Homeward Bound

**Chapter 15 Notes:** Dean and Jess head to Stars Hollow. Some Stars Hollow happenings may occur outside the original timeline of events. Thanks to everyone who is still reading and reviewing. I really appreciate every review I get.

 **Disclaimer:** I own nothing except my own obsession with Gilmore Girls.

 **Trigger Warning:** Homelessness. Mentions of 'off camera' domestic violence.

Jess clocked out for his break and ducked into the hallway leading to the loading dock, pulling his cell phone out of his pocket and hitting the speed dial button for Luke as he walked. It rang three times before the call was picked up. Jess heard a cacophony of loud talking and clanging silverware before his uncle came on. "Hey Jess! Gimme one second." Jess listened as Luke yelled something to Caesar. When he came back on the phone, the background noise was gone. "Ok. I can hear you now. What's up, nephew?"

"Sorry, is this a bad time?" Jess had purposely waited to take his break until around two, when he thought the lunch rush at the diner would have died down, but he still felt guilty for pulling Luke away from an obviously crowded diner.

"What? No, of course not."

"You sure? It sounds like it's busy over there."

"It's fine. It's a little busier than usual for this time of day, but Caesar and Lane can handle it. If they don't kill each other first." Luke laughed. "Are you on your lunch break?"

"Yeah, I am."

"You've been calling on your lunch break a lot lately."

Jess waited a beat. "Is that not ok?"

"Of course, it's ok, Jess. I always want to talk to you whenever it's good for you. But, don't you need that time for, you know, eating your lunch?"

"I get an hour. It only takes about five minutes to scarf down a sandwich."

"That doesn't sound good for you." Luke scolded. "I love getting a surprise call from you when I'm at work. But, I do kind of miss your Sunday night calls, too. When I'm home on the couch and relaxed with a beer."

Jess hadn't expected to get called out on the change to his routine. He had stopped calling Luke on Sunday nights around the time he learned that his uncle was dating Lorelai. It had felt safer to call when he knew Luke would be at work, and he only had diner customers to compete with for his uncle's attention. He couldn't stomach the idea of catching Luke with Lorelai and having her eavesdropping on Luke's side of the conversation and either asking questions about Jess, or outright mocking him, once they had hung up. Or even worse, having Luke brush him off because he was with Lorelai, rushing him through the call to get back to her, or not fully paying attention to what Jess was saying because he'd rather be talking to Lorelai. He thought it was better not to risk that when the mere idea of it hurt him already. "I'm sorry. I guess, I just kind of figured I have more privacy when I call from work now. I mean, me and Dean are pretty much on top of each other at the apartment….and I figured it might be more convenient for you now, too…."

"What do you mean? You think I'm out painting the town on Sunday nights?" Jess could hear the sarcasm in Luke's voice. But, also, maybe, a little bit of hurt. It occurred to Jess that Luke might be worried about being blown off, too.

"I guess I didn't want to intrude if you were entertaining your lady friend in the evenings."

Luke laughed at Jess' phrasing. "I do spend some evenings at Lorelai's house, and she spends a few over here. Though, not as many. She's pretty stuck on always wanting to be at her place. But, that doesn't mean you can't call me. You know that, right?"

"Uh, yeah, sure. I just didn't want to cramp your style. Your relationship with Lorelai was years in the making. I don't want to mess it up for you by getting in the way of whatever you two crazy kids are getting up to on a Sunday evening." Jess tried to lighten the mood before he got too mentally bogged down by this latest manifestation of his fear of being rejected.

Luke countered with increased seriousness. "Jess, you are never in the way." He lightened his tone slightly. "Do you have any idea how many times Lorelai talks to Rory on the phone when we're together?"

"Ummm, I'm going to go out on a limb here and say a lot?"

"You bet, a lot. Sometimes several times in one night. If she's on a date that's not going well and wants Lorelai's advice. If Paris is driving her crazy. If some guy is sitting in her spot at her study tree. And Lorelai always picks up, and always talks to her for as long as Rory needs to talk."

"Hmm." Jess mused. "Is my takeaway from this supposed to be that Rory is worryingly codependent, or that Lorelai has poor dating etiquette?"

Luke chuckled. "Neither, smart-ass. My point is just that Rory always comes first with Lorelai. And I understand that because she's her kid and she should. Rory should be her top priority. And Lorelai understands that it's the same with me and you. She wouldn't mind if you called while she was here or while I was at her place or whatever. I'm just saying you can call me whenever you want. Always. Lorelai fits the rest of her life around Rory and she gets that I do the same with you. Ok?"

Jess thought Luke was greatly overestimating Lorelai, in terms of both the level of respect she had for his relationship with his nephew and her ability to quietly entertain herself while Luke was on the phone. Not that this surprised Jess. After all, Luke had been overestimating him from the moment he had stepped off the bus in Stars Hollow. That thought made Jess remember the reason he had called to begin with.

"Ok. If you say so, Luke."

"I say so." Jess could hear the smile in Luke's voice. "I like it when you agree with me without a fight. You should do that more often."

"Well, today's your lucky day, because not only is your favorite nephew agreeing with you, but he's also coming to Stars Hollow to visit you this weekend." Jess paused waiting for Luke's reaction and when none came he added. "If that's all right?"

"Of course, it's all right, Jess! It's more than all right. I'm just surprised. When are you coming?"

"Uh, we're going to take a bus out on Saturday morning and get to Stars Hollow around eleven. Then we'll take a bus home late Sunday afternoon."

"We? Is Dean coming with you?"

"Yeah, Dean and Clara both. Clara has a slumber party to go to for her best friend's birthday on Saturday. Her aunt was supposed to take her, but I guess she broke her wrist and can't drive, so Dean is going to bring her, and I figured I might as well tag along and see you…if you don't already have plans, that is…."

"I don't have plans. I can't even think of any plans that your visiting wouldn't trump." Luke paused. "Oh, uh, there is one thing you should know."

Jess' stomach clenched, afraid he was about to be at least partially blown off for Lorelai. "Yeah? What's that?"

"Rory is coming home this weekend. It's the start of her spring break. But, I know Lorelai set her up with a job doing inventory or something for Andrew at the bookstore. So, she should be busy and everything…...but maybe you guys want to avoid the bookstore, just in case."

Jess sighed. "I'm pretty sure Dean normally avoids bookstores anyway and I'm a big boy, Luke. I'm not going to fall apart if I happen to cross paths with Rory Gilmore while I'm in town. With you dating Lorelai, I'm guessing it will happen at some point. And it's probably less awkward if it's before she's dressed as the maid of honor and I'm pretending to be the best man, right?"

Luke didn't answer right away, and Jess got irritated at himself for planting wedding ideas in Luke's head. "Not that there needs to be any rush to the altar or anything." Jess smirked. "Just use a condom and you'll be fine."

"Watch it, Jess. And I know you're not going to fall apart. I just worry about you…and you and Dean have become such good friends now. I'd hate to see something happen with you guys."

"I can't speak for Dean, but I promise you that I'm not going to start swinging at him just because Rory's in town. Ok?"

"Ok, Jess." Luke didn't sound convinced and Jess felt himself getting annoyed.

"Jeez, Luke! Give us a little credit here. We're adults. We'll be fine." Even as Jess spoke, his stomach started to tense as he remembered Dean's drunken, hateful words about Rory never really loving or trusting Jess. The picture of Rory on the couch that Dean had brought back from his aunt's house. His own memories of her and his recent desire to share his manuscript with her. How he had left things the last time he had seen her before he had run off to California. He felt a wave of regret knowing that bit of bad behavior would give Dean a leg up, quickly followed by shame at the realization that part of him still saw this as a competition.

"Ok. Ok. I'm sorry. You're right. I'm sure everything will be fine."

"Wow, your faith in me is really overwhelming. I may just get emotional."

Jess listened to Luke chuckle softly. "All right. I'm sorry, kid. I just worry about you."

"I know you do." He did know. It was the thing he appreciated the most about Luke, and also the thing that annoyed him the most about Luke. "So, it's cool if Dean and I stay with you, right? I told him it was, but he wanted me to double check with you."

"Of course, it's ok! Where else would you guys stay? Dean will be ok with the couch, right? If Rory wasn't home, I'd stay at Lorelai's and give Dean my bed, but I haven't spent the night over there when Rory's been home yet…"

"Dean's fine with the couch. Or, I don't know, maybe he's too tall for it, but I can take the couch. We'll work it out. We're not going to kick you out of your place. Plus, who would make us pancakes in the morning if you slept at Lorelai's?"

"Good point, nephew." Jess absorbed the warmth Luke infused in those three little words.

"Hey, my car still runs, right?"

"Huh? Yeah, it does. I go over and start it up every few weeks. I was over there last week, and it started up fine. Why?"

"I told Dean he could use it when he moved back to Stars Hollow. He just realized he would need a car out there and started freaking out about it."

"Yeah? That's a good idea. Someone should be using it. It's just been sitting in storage collecting dust. I'll look into what it will cost to put it back on my insurance plan. That's probably the cheapest way to do it since my name is still on the title."

"Hey, Luke." Jess wasn't sure how to bring up something that had been bothering him since he had talked to Dean about the car. "How come you stole my car last year?"

"What? You know why!" Luke chuckled. "It was part of my master plan to keep you from driving out to Walmart to work when you should have been in school."

"I get that. I guess, what I mean, is." Jess wasn't sure why he felt the need to bring this up. "Why didn't you just take my keys away or, I don't know, ground me or something? Wouldn't that have been more normal?"

Luke spoke slowly, as if he was still thinking over what to say. "Why didn't I ground you? I don't know. I, uh, I guess I didn't think of that as an option."

"You never even considered it before you stole my car?"

Luke sighed. "Yeah, I considered it. Grounding someone only works if that person is willing to follow the rules and be grounded. And, I guess I didn't think you'd let me ground you. Back then, you could be kind of…." Luke trailed off as he searched for the right word.

"A shithead?"

Luke huffed out a quiet breath, barely a laugh. "I was going to say difficult, or stubborn maybe, but ok, I like your word, too. And I know stealing your car was pretty out there in terms of parenting strategies, but I guess I saw it as the safest option, you know, like a way to get the result I wanted and still avoid the direct confrontation of trying to ground you. I was already telling you to go to school and you weren't listening to me. I thought it would only escalate things if I tried to ground you and you didn't listen to me about that either. Does that make sense?"

"I guess so."

"Why are you asking me about this now?" Luke's voice held concern along with curiosity. "What brought it up?"

Jess shrugged, then realized Luke couldn't see him. "I was telling Dean about my car the other day. He was surprised I still had it because he had heard it was stolen, so I told him about you stealing it and why you did it and he asked why you hadn't just grounded me or taken my keys away instead. And, I don't know, I guess it got me thinking about why you didn't. I was just curious, I guess." Even though Jess had come up with the same reasoning on his own and he knew he hadn't always behaved in the most trustworthy manner when he had lived with Luke, he still felt surprisingly hurt and embarrassed to hear how little his uncle had trusted his eighteen-year old self.

"Hey." Jess could hear the lame joke coming in Luke's voice. "If you're feeling like you got short-changed, I can always make it up to you when you're home this weekend and lock you in your room and send you to bed without dessert or something." Jess smiled as he heard his uncle laughing at his own wit.

"Hmmm, I think I'll pass, but thanks for the offer." When Jess spoke again, it was hesitantly. "You do trust me now, though, right?" He asked. "I mean, I get why you didn't trust me then. But, you do trust me now, don't you?"

Luke didn't hesitate. "Yes, of course I do, Jess. Completely."

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Luke was still thinking about his conversation with his nephew later that night while he was standing at Lorelai's stove cooking dinner and listening to Lorelai chatting on the phone with Rory as she flipped through a magazine at the kitchen table.

"I cannot wait to see you, kiddo! It's been way too long this time!"….."No, only three weeks? I don't know what kind of crazy math they're teaching you at Yale, but that doesn't sound right to me at all…."

He thought about Jess feeling like he couldn't call in the evening anymore because Luke might be with Lorelai. Luke had done his best over the past three years to make Jess realize he was loved, and that no one in Luke's life was more important to him than Jess was. He knew they had made great strides in their relationship, especially after California. Luke had thought he had lost Jess for good, then, when the boy had run off without a word. But, when he had returned, sad and hurting from being let down by a second parent, Luke had told Jess that he loved him for the first time. And he had kept telling him. Along with a 'good night' before he went to bed at night. Along with a 'have a good day' when Jess was leaving the apartment in the morning to do whatever it was he did during the day. Until, finally on the day Jess left for New York, Luke heard it back. The distance between them after Jess moved out and the infrequency of their conversations gave Luke the confidence to capitalize on this new development, ending every conversation with an I love you and every visit with a hug to accompany it.

"…and, another day we'll get make-overs, and we'll need to have at least one movie night, maybe four, now that I'm really thinking about it. I have a bunch of rentals that are overdue because I started watching them and then stopped, thinking this was such a Rory movie that I needed to save it to watch with you."…"oh, lots"…"very, very overdue"…"As in, take out a small loan to cover the late fees overdue." Luke heard the smirk in his girlfriend's voice. "Don't fret, my pet. Kirk is working at the movie rental place this month. Who knows how to handle Kirk better than me?"

Luke knew saying it wasn't enough to make a kid feel loved. He remembered Liz calling in the middle of the night once during Jess' junior year, drunk and needy and begging Luke to wake Jess and put him on the phone so she could tell her baby boy how much she loved him. He knew Jess had probably heard that from his mother throughout his childhood, even as she repeatedly put husbands, boyfriends, alcohol and drugs above her son. Luke knew kids needed to be shown they were loved. He thought he had done that, too. Being there for Jess when the boy had lived with him, sticking up for him in town, always making time to talk to him and sit down to meals with him. Introducing him to Nicole when they had been dating. Calling to check in on him in New York. Regularly going into the city he hated to visit him. But, days like today, he got the unnerving feeling that it was all too little, too late.

He thought about Rory, who had never had to spend one day of her childhood questioning whether she was loved. Sure, her father was a deadbeat loser, but she had always had Lorelai, enthusiastically and effusively adoring her. He thought about his own childhood. He didn't know if it could be classified as a particularly happy one since he had lost his mother so early, and his father so soon after reaching adulthood. But, he had always known he was loved when he had them. He thought about Dean and Clara, and how they had lost their parents young, too, and about what good kids they were despite their loss. He knew they had been loved children. He thought about how difficult life could be even with that solid foundation. He couldn't imagine struggling through life without it. With parents alive and out there in the world but not really interested in their child. A mother who couldn't get her own act together enough to love her son and a father who couldn't be bothered to even try. He didn't know how a kid was supposed to recover from that kind of childhood. How they were ever supposed to really believe they were loveable.

"And, I want us to have dinner one night with my new beau."…"I think you'll like this one."…Luke turned to look at Lorelai, and she winked at him. "He might just be a keeper." Luke smiled at his own good fortune. He knew he was no prize himself, and he was still amazed everyday that Lorelai was dating him. "Uh-huh."…Lorelai grinned wickedly….."Me too."….."Hey, I wasn't being dirty! I can't help it if you have a dirty mind!"….."I miss you. Every second of every day."…"All right, kiddo, see you tomorrow at Friday night dinner and then for a week straight with no Yale or grandparents to get in our way!"….."I love you, too."…"Put your pants back on, Luke! I know you like to cook naked, but not in front of Rory! Have some decency!"

Luke immediately defended himself, loud enough to be heard on the phone. "I have pants on, Rory! I always have pants on! I even shower with them on when I'm over here-" Luke whirled around and stopped talking when he noticed Lorelai's cell phone, the screen dark, laying a foot away from her on the table. "You know I hate that joke." He tried to sound stern. He really did hate that joke.

"I know, but I love it. And you're too easy!" She smirked wickedly at him, and he felt his annoyance waning. He leaned over and kissed her before turning back to the stir-fry in the pan in front of him.

"You're lucky you're so charming." He spoke over his shoulder.

"I certainly am. Charm is how I plan to get out of my late fees at the movie store. So, how about it, boyfriend. Are you up for having dinner with Rory one night this week when she's home?"

"Of course, I am. I'm always up for spending time with Rory. You know that."

Lorelai got up and stood behind Luke at the stove, wrapping her arms around his waist as he moved the tongs around the pan, browning the strips of chicken breast.

"I do know that. I raised a pretty great kid, huh?" Luke could feel Lorelai's face move against his shoulder as she smiled.

"You did indeed. I'm really looking forward to seeing her. Did I tell you I read an article about Yale architecture in a magazine the other day?"

Lorelai laughed lightly, not mocking, just tickled. "What were you doing with an architecture magazine?"

"A customer left it behind at the diner. I would have just tossed it, but it was open to this article on Yale, so I read it. I feel like now that Rory's an adult, I need more to talk to her about than just how's school, you know?"

"So, you two are going to have a serious discussion about Yale architecture?" Luke turned his head to see the top half of Lorelai's face peeking over his shoulder, one eyebrow raised and her arms still tight around him.

He chuckled. "I don't know. Maybe we will."

"I'm not sure if that girl has poked her head out her books long enough to notice that Yale even _has_ architecture."

Luke laughed. "Perfect, then I can tell her all about it." He smiled at Lorelai and leaned in for a quick kiss, then turned pack toward his frying pan. "Oh, hey, Jess and Dean are going to be in town this weekend, too. They're getting in on Saturday morning and leaving Sunday afternoon."

"Oh, yeah?" Lorelai released Luke and took a couple of steps back.

"Yeah, I guess Clara has an overnight birthday party here in town and they're bringing her out on the bus."

Lorelai laughed. "An 'overnight birthday party'?"

"What?" Luke could sense the mocking in Lorelai's tone now. "What's wrong with that?"

"Nothing. You're just funny. Most people would just call it a slumber party."

"Ok, a slumber party. Whatever." Luke hated the tension that always arose when he brought Jess up in conversation. The worst part was he could no longer tell if it was Lorelai's reaction to Jess, or his own preemptive reaction to the reaction he expected to get from Lorelai. Either way it was exhausting.

"Ok. Well, then. Why don't we each do our own thing this weekend with our respective special guests and then talk about a plan for having dinner with Rory one day next week. Maybe you can even join us for your first ever Gilmore Movie Night." Luke knew it wasn't rational to feel rejection in Lorelai's plan. It's not like he had been expecting Lorelai to invite Jess and Dean over for a family dinner or anything. That would have been much too awkward and complicated with all three kids and their combined histories. And he did understand that Lorelai had a reason to be distrustful of Jess after the way he had just taken off on Rory when they were dating. Maybe Jess would get a chance to apologize for that this weekend and wipe out some of Lorelai's residual anger toward him.

Luke looked at Lorelai carefully before responding. "I've watched movies at your house before."

"Ah, yes, but a movie night isn't a true Gilmore Movie Night unless both Gilmore girls are in attendance and there are copious amounts of junk food eaten! I'm talking more than you've ever allowed yourself to indulge in at past movie nights. I'll make Rory be the junk food pusher. I know you can't say no to Rory!"

Luke smiled at her, relieved to feel the tension gone. Rory wasn't the only one he couldn't say no to.

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Jess was having trouble concentrating on his book. He knew he should give Dean the same fair warning that Luke had given him, but he wasn't sure how to bring it up without making it into a much bigger deal than it needed to be. That's why they were about an hour out of Stars Hollow and he still hadn't said anything. He shut his book on his finger to save his place and looked over at Dean across the aisle. Dean was looking out the window over Clara's head, while she quietly read a book in the window seat. He hoped she would keep reading and not pay attention to their conversation. He had really hoped she would fall asleep on the bus. Wasn't that something kids did? Get lulled to sleep in cars and on buses, and other modes of transportation. Maybe she was too old for that. He sighed. And maybe he was stalling.

"Hey, Dean." Jess knocked the back of his hand against Dean's arm to get his attention.

Dean looked over and covered his mouth as he yawned loudly. Of course, Dean would be the one who got sleepy on the bus. "What's up?"

"So, uh, I know this isn't a big deal or anything, but I wanted to let you know that Luke told me that Rory is going to be home this weekend, too. I guess it's the start of her spring break and she's spending the week in Stars Hollow."

"Oh, uh, ok."

Jess tried to mirror Dean's blank expression, but Dean had surprise on his side. Jess had been worrying about this conversation for almost two days before he started it. He looked past Dean, out Clara's window. "I guess she's going to be working at the bookstore or something. Anyway, I just wanted to let you know. I'm not really sure why. I think Luke is worried about it, about us running into her or something, and it being weird for us. I don't know.….." Jess knew he was rambling but wasn't sure how to end the conversation. He felt awkward and embarrassed for letting Luke get into his head about this and make it into something bigger than it should have been. "So, whatever. Now you now."

"Ok. Thanks for telling me. What is Luke worried about?" Dean smiled, but it looked a little less natural than usual to Jess. "Does he think we're going to start fighting over her again or something?"

"I don't know. Something like that. You know how he is-"

"Who?" Clara looked up then, concern on her face at catching the tail end of the conversation. "Who are you going to start fighting over?"

Dean turned to his sister. "We're not going to fight over anyone. Rory is going to be home this weekend and Luke is worried about us running into her."

Clara grinned. "Rory's home! Can we go see her? That would be so fun!"

"Uh, I don't think that's a good idea, Clara. Plus, you're going to be busy with your friends and your slumber party."

Clara frowned. "What about Lindsay, then? Can we at least go see her? Maybe we could just go by after the party tomorrow? I miss her."

"Maybe." Dean relented. "I can see if she's free." Clara grinned happily. "No promises, though, ok. I'll see what I can do."

"Ok, Dean." Clara focused her attention back on her book, a small satisfied smile on her face. Jess watched, impressed that the girl already knew how to work Dean. Ask for the thing that's really off the table first and end up getting what you really wanted all along. Jess wondered how Dean would hold up when he was her actual guardian.

Dean looked back to Jess. "If you're still into Rory, you don't have anything to worry about from me. I mean that, Jess. Ok? After everything you've done for me, I would never stand in your way. I want you to know that."

"What? Oh, uh, no, it's not like that." Jess fumbled his words. "We haven't even seen each other since I took off for California without saying goodbye. I'm pretty sure she hates me now."

Dean was shaking his head slowly, a small smile on his lips, and concern in his eyes. "I doubt that. Now that I really know you, I don't think you're very hateable at all."


	16. Chapter 16 - Stars Hollow Part I

**Chapter 16 Notes:** Jess and Dean are back in Stars Hollow. Some things get resolved for the better. The timeline of certain past events may be a little blurred here. I think this is the homestretch. I'm thinking there are only two or three more chapters til everything is wrapped up. Thanks to all you lovely readers and reviewers who are still following this story. I hope this chapter doesn't disappoint.

 **Disclaimer:** I own nothing except my own obsession with Gilmore Girls.

 **Trigger Warning:** Homelessness. Mentions of 'off camera' domestic violence.

Walking through Stars Hollow with Dean felt weird to Jess. It felt surreal and absurd in a way that being with Dean in New York didn't, not anymore at least. In the time it had taken them to walk from the bus stop to Sabrina's house to drop off Clara, and then to the diner, several townspeople had greeted Dean, just Dean, with smiles and waves, welcoming Dean back and telling him it was good to see him. Jess had either been ignored completely or the recipient of not-so-welcoming looks, some puzzled at the sight of him with Dean and others as disdainful as if they had stepped in dog shit. Then there had been the run-in with Taylor, who had accosted Dean on the sidewalk to talk about the letter of recommendation Dean had called him about and to inquire as to whether Dean was still looking for work and an apartment in town. When the man noticed Jess standing off to the side, patiently waiting, he had asked Dean in a stage whisper if Jess was harassing him and if he needed Taylor to call the authorities for him. Dean had laughed it off and thanked Taylor, agreeing to come by Doose's later to pick up the letter and discuss his plans, but it had rankled Jess. They were a few yards from the diner when Jess felt a solid grasp on his arm, effectively bringing him to a halt. He looked up, his alarm turning to confusion as he took in Dean's concerned expression. "What?"

"Are you ok, Jess?" Dean took his hand off Jess now that he had his attention.

"Uh, yeah. I'm fine. What are you talking about?"

"You've had this look on your face since we got off the bus. Like you're pissed or really frustrated or something. You look like you're ready to blow. I haven't seen you look like that since high school. Are you sure you're ok?"

Jess thought about that. He knew he regressed somewhat back into his angry younger self whenever he came back to Stars Hollow. He had felt his walls going up as soon as they had started walking through town, but he hadn't realized he had been so obvious. "Yeah, I'm ok."

"Yeah? Then why is your scowly-face back?" Dean smiled at the reference, trying to get Jess to do the same. "And why did I have to grab you to get your attention? I said your name like three times and you were totally zoned out."

Jess frowned. "Really? Sorry. Just thinking, I guess."

"You sure you're all right?"

Jess forced a small smile onto his face and nodded, but he decided to be honest when he could tell Dean wasn't buying it. "Look, Dean. This isn't exactly my happy place. Aside from Luke and Rory, everyone in this town hated me, you included. I'm not saying I didn't bring it on myself. I know I was a jerk when I lived here. But, it's just hard coming back here for me and facing that. How I was then. How people here still see me because of it. I have some good memories." Jess thought about how many of those good memories revolved around Rory, and how stupid he had been to just walk away from one of the few good things he had ever had. "I mean, I got Luke out of it." That was true, of course, but Jess felt a twinge of guilt knowing it wasn't the whole story. "And being here with him definitely beat a lot of my living arrangements prior to being in Stars Hollow, but it still wasn't a very good time in my life, and it's hard being here and remembering how I felt then." He looked past Dean, staring at the town square. "So, I'm sorry if I'm not good company this weekend, but I'm doing my best."

Jess felt Dean's arm along his back and a light squeeze on his shoulder as Dean pulled him into a one-armed half-hug. "Hey, you're always good company." Jess tried to be subtle so as not to offend as he instinctively extricated himself from Dean's casual embrace. "And I get it. I really do. Having even the good memories of living here linked to the bad ones."

Jess felt himself warming with shame at not having thought about how difficult being back here had to be for Dean. All the good he had experienced here couldn't possibly come close to outweighing the loss of his parents. But, Jess had been too preoccupied with his own shit to think of Dean. Jess looked up, feeling guilty and ashamed, and so very disgusted by his own selfishness. "I'm an ass. I'm so sorry, Dean. I wasn't thinking….."

Dean huffed out a breath, shoving his hands in his pockets to keep from reaching out to Jess again. "You're not an ass. I get that stuff wasn't easy for you when you were here either. You were dealing with a lot of shit back then."

"My shit is nothing compared to your shit." Jess looked at the ground in front of him, then back up at Dean. "Don't think I don't I know that."

Dean shook his head, and fidgeted with the strap of his backpack, adjusting it on his shoulder. "That's not true. If I had known about stuff with your mom back then…..well, I would have been a lot less of a jerk to you." Dean smiled tentatively at Jess. "Or I would have tried to, at least." He smiled and tilted his head toward the diner. "Should we go in?" His stomach growled loudly, and both boys laughed. "I guess I'm a little hungry."

"Ya think? When are you not?"

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"There they are!" Dean followed Jess into the diner and watched his friend get instantly swept into a hug by his uncle, feeling a pang as he remembered his parents, excitedly welcoming him home when he returned from a week long hockey camp over winter break his senior year. He tried not to let his mind linger on the things he would never have again. He really did. His parents hadn't raised him to dwell on the negative. But, it was so much harder to stay positive without them.

"Jeez, Luke!" Jess groused, barely allowing himself to be hugged before pulling back, and putting space between himself and Luke. "Let me at least walk in the door before you jump on me!" Dean recognized it for what it was, Jess' knee-jerk defensive reaction to affection, like the way he had pulled away from Dean's touch outside. Dean understood that physical affection was a bigger deal for Jess than it was for him. Dean was pretty much open to hugs from people he liked all the time. He connected touch to love and affection in a way he knew Jess didn't. He knew Jess had been uncomfortable the night he had hugged him in the apartment, but he had still let him do it. And, he had seen Jess willingly hug Luke back in New York, so he assumed the venue change was the cause of Jess' hostile reaction, that it was too hard for him to bear when he already felt stressed being back in town. Dean hadn't taken Jess' reaction personally, and he was pretty sure Luke wouldn't either.

"Sorry, Jess. I was just setting down Kirk's BLT right here." Luke waved his arm toward the table a few feet away where Kirk sat by himself, sandwich untouched as he stared up at them with open interest. "And I turn around and you're walking in the door! I'm so happy to see you guys!" Luke's grin was contagious, and Dean found himself smiling widely. "Get over here, Dean. It's good to see you!" As Dean leaned in to hug Luke, he heard Kirk say hi to Jess.

"Hi, Kirk." Jess responded.

"So. Is it true?" Kirk asked, face expressionless. "Were you really sleeping in an actual gutter when Dean rescued you in New York, or is that just an expression people use?"

"What? Jeez, Kirk!" Jess stared murderously at Kirk. "No, I wasn't! How about you mind your own damn business!"

Kirk's expression was blank as he turned toward Luke. "Luke, I can't enjoy my lunch with your nephew directing his hostility at me like this. It's not good for proper digestion"

Luke sighed. "Kirk, either leave Jess alone, or go enjoy your lunch outside. Jess, c'mon." Luke put a hand on his nephew's shoulder and tried to steer him toward the counter. "Come eat. What do you guys want for lunch?"

"Hi Sweetie, welcome back!" Miss Patty walked through the door behind them. Jess glared at her, and she looked his way, the smile fading from her face. "Oh, I was talking to Dean. But, look, you're here, too, Jess. Isn't that nice?"

"Whatever. I'm going upstairs." Jess grabbed his half-full duffel bag off the floor where he had dropped it when Luke hugged him and headed for the staircase.

"You're not gonna eat?" Luke called after him.

"Not down here I'm not!" Jess called over his shoulder as he stalked off toward the stairs.

Dean watched Jess go, worried at his over-reaction and wondering if Jess was going to be this angry until they were on the bus out of town the next day. He turned back toward Kirk and Miss Patty, and spoke clearly and slowly. "It was an alley. Not a gutter. And _I_ was the one sleeping in it when _Jess_ rescued _me_ in New York." As Dean looked over toward the curtain behind the counter that Jess had disappeared behind, he heard Babette, in a voice he knew she thought was a whisper, saying 'the poor little thing' as Miss Patty joined her at her table.

Dean turned to Luke. "Should I go make sure he's ok?"

"You might want to wait a few minutes, Dean. Give him some time to calm down." Dean felt Luke's hand on his back and let himself be gently guided toward a seat at the far end of the counter. "Come sit over here for a bit. How about I make you guys some lunch and you can bring it up to him? What would you like?"

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Jess lay sprawled across the couch, his body tense with annoyance. He was annoyed at this stupid town. He was annoyed at himself for coming back and subjecting himself to this stupid town. But, most of all, he was annoyed that this stupid town could still make him feel this annoyed. He thought he had moved past feeling like this. He felt like he was on his way to getting his shit together in New York. To being an emotionally stable adult who was capable of taking care of himself. A responsible employee. A good nephew to Luke and good friend to Dean. Someone who didn't hate himself quite so intensely that he felt like he was constantly drowning in feelings of worthlessness. Then, twenty minutes back in this ridiculous town and all that progress flew out the window, leaving him back at square one, exactly who he had been a year ago. An angry, volatile teenager with self-esteem issues who can't play well with others or get along in civilized society without exploding all over everyone. And thinking about Rory. He knew everything was heightened this time knowing that Rory was in town. The last time he had been back to Stars Hollow at been at the end of the summer, when Rory was safely an ocean away, traipsing through Europe with her mother. Now, he was on edge that he could run into her at any moment. He had gone over what he would say to her if he ever saw her again a million times in his head. And, now, with Luke and Lorelai dating, it was inevitable that he would see her again, if he wanted to remain in Luke's life. Part of him felt like tracking her down right now and getting it over with and the other part was hoping he could delay seeing her for so long that everyone would have moved on and his leaving the way he did would no longer be an issue, but he knew that wasn't realistic. He knew he had been a coward when he had left without saying goodbye, and he knew he was still being a coward now, and he hated himself for it.

He heard a soft knock on the door. His first instinct was to push Dean away, too. Yell that the door was locked and what the fuck did he want anyway. To just stay up in the apartment and hide from everyone. But, he knew he couldn't do that. Dean didn't deserve it and Jess knew he would regret it. He took a deep breath to get himself under control. "You can come in. It's not locked." He called. The door opened slowly and Dean made his way into the apartment juggling two plates of burgers and fries, with two bottles of ice tea and a bunch of napkins tucked into the crook of his arm, his backpack still slung over one shoulder. Jess quickly got to his feet, feeling like an ass. Again. He sensed that was going to be the theme of the weekend for him. He grabbed the two plates from Dean and set them down on the table. "Sorry, I didn't realize you had your hands full like that."

"No problem. Thanks." Dean smiled as he put the bottles down, one by each plate, tossed the napkins on the table and dumped his backpack on the floor. He turned in a slow circle, taking in the apartment. "It's nice up here. It's bigger than I pictured."

"Yeah. It was smaller when I first got here." Jess pulled out a seat and sat down in front of his burger, watching Dean look at his former home. "Then Luke bought the building next door, so he could knock down the wall and expand the apartment."

Jess grabbed and fry and stuck it in his mouth. He looked up at Dean who was now staring at him in surprise. "What?" Jess asked. "Hey, thanks for bringing the food up by the way."

"Yeah, no problem. So, Luke bought a whole building just so he could give you your own room?" Dean asked the question slowly, trying to digest the concept even as he said the words.

"Well, my own area of one larger room, I guess." Jess shrugged. "I didn't get a door, so it's not technically a room." Jess watched Dean nod his head, still taking in the apartment. "You can look around if you want."

"Yeah? Thanks." Dean wandered over to Jess' area of the apartment. "This is your room?"

"Was my room. I'm not planning on ever living here again." Jess started on his burger as Dean walked through the apartment to Luke's side, keeping a respectful distance as he peeked in. He looked into the bathroom, too, and then circled back to the table and sat down in the chair next to Jess.

"It's a really nice place." Dean looked at Jess. "It completely blows my mind that Luke bought the building next door so that he could give you your own room. That's so….nice."

"I'm sure he did it for himself, too. I wasn't exactly a joy to be around back then, if you recall. I'm guessing he wanted space from me as badly as I wanted it from him." Jess thought about the early days of living with Luke. The inflatable mattress that was meant for him, but that Luke had slept on that first night because he wanted Jess to have the bed so that he would feel at home. All the times Luke had let him blast his music at night because he needed it to get to sleep. All the conversations Luke had tried to have with him even though all he got for his effort was sarcasm and attitude. He thought back to his conversation with Dean at the pizza place and it occurred to him that he sometimes downplayed what Luke had done, and continued to do for him, in the same way he downplayed what he himself had done for Dean. He reflected on this for a moment, wanting to give Luke credit. It's true he hadn't gotten a proper room with a door, but Luke could have just put him on the couch, with no privacy at all. He could have told Liz no to begin with because he didn't have room for a teenager or he could have sent Jess back to New York when he got tired of dealing with his shitty attitude. "But, yeah, it was really nice of him."

"Definitely." Dean dug into his burger, chewing thoughtfully, and wiping his mouth with a napkin. "Oh, Luke said to tell you that he'll be done in the diner in about an hour or so. He said he has to work the lunch shift because Caesar is out sick today. But, then he's going to close up for the afternoon so he can spend time with you, and he wants us to have dinner together tonight."

Jess just nodded in response, as he ate.

Dean's expression grew serious. "It's crazy to think that I might be back here soon. Living in my own apartment with Clara."

"Are you scared?" Jess asked hesitantly. "Or nervous, at least?" Jess felt a wave of shame that Dean was willing to take on something so huge, while he couldn't even muster the courage to face his ex-girlfriend.

"Um, yeah, I'm terrified!" Dean laughed uneasily. "I'd have to be an idiot not to be, right?"

Jess nodded. "Yeah, definitely. I would be pretty freaked out in your situation. Clara was asking me about that when you were in the bathroom at the museum last Sunday."

"About me being scared?"

"Yeah. She could tell you were scared and she was worried that you'd change your mind about trying to get custody."

Dean frowned. "What did you say?"

"I pretty much told her what you just said. That you were scared. That you'd have to be an idiot not to be. Then I told her, lucky for her you're an idiot, so you wouldn't let that fear stop you." Jess grinned and took a big bite of his burger.

Dean shook his head, smiling. "You did not! You're an ass, but you're not that much of an ass."

Jess finished chewing. "I may have paraphrased a little bit to make it more inspiring." He shrugged. "Who can remember?"

"Hey, after you went upstairs, I told Kirk that I was the one sleeping in the gutter, not you." Jess could feel Dean watching him for a reaction as he slowly chewed a fry, eyes on the plate in front of him. "Miss Patty and Babette heard me, too, so I'm guessing that story will sort itself out soon."

"Whatever. I don't care what any of these people think. Least of all Kirk, who can barely even think to begin with."

"Ok. I just figured if they're going to be gossiping about what happened, they should at least have their story straight."

"It doesn't matter. It won't change anything. They had their minds made up about me a long time ago."

"Stuff changes, Jess. We're proof of that. I had my mind made up about you a long time ago, too. I hated you. I pretty much wanted to kill you that night at Kyle's party."

Jess huffed out a breath of air and looked up at Dean. "Yeah, I got that."

Dean smiled. "And, now, I'm really glad I didn't kill you that night, because you're my best friend." Dean paused. "It takes time, but stuff can change."

Jess nodded wordlessly, feeling inadequate, knowing he should probably tell Dean that he was his best friend, too, but unable to bring himself to say it. The thought of it made him feel too vulnerable, and exposed. And Dean didn't look like he expected anything from him, but still, he knew he needed to say something back. "You can take my old bed tonight if you want. I'll take the couch. And before you give me shit about it, you should check out how small the couch is."

Dean glanced into the living room. The couch was small, more of a loveseat size really. He would never fit comfortably on it. "I can just take a blanket and sleep on the floor or something. I'll be fine. I don't want to kick you out of your bed."

"It's fine. I've napped on the couch before. I can fit." And when Dean started to object, Jess cut him off. "Seriously, I _want_ to sleep on the couch. I will fight you for the couch if I have to." Jess said without heat, eyes down on his plate as he dunked a fry in ketchup. "You haven't slept in a real bed in a long time. Just let me be nice to you. Ok?" When he looked back up, Dean was smiling softly at him.

"Ok, Jess. Sure. Thanks."

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Jess stood outside the bookstore, trying to decide what to do. He knew he needed to talk to Rory. He needed to apologize for the way he had left things last year. It was the only way to get past the bone deep shame that burned through him every time he thought about Rory or California or that time in his life. It was the only way he would ever be able to come back to Stars Hollow without being consumed by anger and self-loathing. And he wanted to get past it. He did. He was tired of being weighed down by guilt and shame, for this and for so many other things he had done. He wanted to stop carrying that around with him. This seemed like where he needed to start. And he wanted to be able to talk to Rory again. He knew it would probably never be like it was before between them, but he wanted the possibility of having her in his life again, for them to at least be able to be around each other, especially now that Luke was dating Lorelai. He didn't want his issues with Rory to cause any problems there for Luke. He tried to convince himself that that was his motivation here, or at least part of it, wanting to right a past wrong and not cause current trouble for Luke. But, if he had really moved past this, past her, as much as he told himself he had, he wouldn't need to deliberate like this. He would already be in the store. He thought about the first night he had taken Dean home with him. How they had both apologized for how they had treated each other in high school. It had been awkward, but not emotionally charged. He had remembered the idea of hating Dean once, but he hadn't been able to still feel it. The hate had been situational, mostly due to their fighting over Rory. He had meant his apology in New York, and it hadn't been very difficult to move on from the past and become friends with Dean. This felt worlds away from that. Jess knew logically that he owed Rory an apology and that he had to give her one, for her sake, as well as his and Luke's, but emotionally he didn't know if he could survive the conversation.

He was still mulling it all over, when his decision was made for him, and Rory walked out of the bookstore. She stopped short a few feet from Jess, her eyes wide with surprise. "You cut your hair." Jess' brain cringed at his mouth's choice of opening lines.

"Huh? That's what have to say to me? Are you serious, Jess?" Rory was angry, and even though Jess knew she had a right to be, he was startled by how confrontational she sounded. "You leave without saying goodbye, you don't get in touch for almost a year, and when you come back all you do is tell me that I cut my hair? I know I cut my hair! What is wrong with you?"

Rory took a step to the side, and Jess quickly moved to block her path, afraid she was going to run from him now that she had gotten over her initial shock. He stood in front of her, on alert, ready to sidestep if needed to cut off her retreat if she tried to swerve around him, but careful to not take the liberty of putting a hand on her to stop her, knowing he no longer had the right to touch her. "Wait, Rory! Please, I just want to talk to you."

When she made eye contact with him again, the look on her face was so intense that Jess questioned whether it might have been in the best interest of his personal safety to have let her walk away. "Yeah. Well, maybe I don't want to talk to you! Did you think about that? Huh? Why would I want to talk to you now, Jess? You left town, you left the state, you left the whole east coast, without bothering to say goodbye! Like I meant nothing to you. Like I didn't matter at all. Do you have any idea how much that hurt? How hard it was for me to get past that? Do you, Jess? Do you even care about how I felt?"

"Of course, I care, Rory! That's why I'm here. I know I owe you an apology. A big one. And I'm sorry. I am. I'm so sorry. I was such a mess back then. I didn't mean to hurt you the way I did."

Rory rolled her eyes and shook her head sharply, crossing her arms in front of her chest. "But, it doesn't matter, does it, Jess? Because you did. You hurt me anyway."

"I know." Jess realized that Rory had changed, too. He thought about all the times he had been able to charm his way back into her good graces when he had done something wrong. When he had failed to call when he said he would, forcing her to accommodate his schedule, and then surprised her with concert tickets to make everything right, or the time he had shown up at her grandmother's house with a black eye that he had refused to discuss and then lied about to smooth things over. He could sense a new confidence in her now, but it wasn't just that. He could tell he wasn't talking to a girl who would put up with bullshit any more, at least not from him. She had grown a thicker skin where he was concerned. Well, good for her, he thought. She shouldn't put up with bullshit. He wasn't the kind of guy who wanted to bullshit her anymore either, but he wasn't sure whether she would give him the chance to prove that. "Rory, I know I fucked up. And I can't change that. And I know that no matter what I say now, it will just be a pathetic excuse and a pathetic apology. I get that. But, it's all I can do. I'm sorry. I'm so sorry. I was going through shit with Luke, and school and my father, and I could say that those were the reasons why I left the way I did. But….." Jess took a breath. He tried to garner the courage he had felt the night he submitted his story to the publishing company and push past his fear. "I loved you. And it freaked me out and I got scared. And I wasn't very good at facing my fears then. I'm working on that now. And, I know we haven't seen each other or spoken for almost a year, but I still…" He faltered, unable to use love in the present tense. "I still care about you so much. Enough that it still scares me."

Jess saw some of the anger bleed from Rory's expression, the tension loosening around her previously pursed lips and the softening in her eyes. Her arms uncrossed and dropped to her sides. "I appreciate that, Jess. A lot. I'm pretty sure I loved you, too." She visibly swallowed. "And I know we never said it to each other or anything, but I always felt like you felt it, too. But, then when you left like that…" Her voice was gentler now, more vulnerable than angry. "It made me doubt everything. I thought it had all been in my head and that you never really cared about me. You really hurt me." Her voice cracked, and she paused.

Jess felt a flicker of hope at this first glimpse of emotion from Rory. Maybe it wasn't hopeless. "I know. I'm so sorry, Rory."

"And then when I heard you came back and made up with Luke for leaving like that. And that's great, I mean, I'm glad you guys made up. I know you love him and he definitely loves you. But, when you made up with him and never bothered to get in touch with me at all, it felt like you didn't care. Like the only person you cared that you hurt was Luke."

"I'm sorry. The last time I was here you were still in Europe. But, I thought about calling you so many times since then. It was easier with Luke…..I was a complete mess after California. It was pathetic. I showed up crying on his doorstep in the middle of the night with nowhere to go." Jess felt embarrassed by the raw emotion in his voice as he thought about that night, that whole short, painful trip cross country and back. "It was humiliating, but it was so much less terrifying to come crawling back to him because I knew he would take me back, even after what I did. I'm not saying I deserved to have him forgive me, just that I knew he would. He's kind of like a parent, I guess, and I knew he would forgive anything I did and be happy to have me back in this life. There was so little risk with him. We ended up getting a lot closer that summer, after my father totally rejected me and Luke was there for me like Jimmy never was. I knew you had a right to be mad, too, and that you deserved an apology just as much as he did, but I was terrified of having you shoot me down and throw it back in my face. If you hated me for what I did to you…I didn't think I could take knowing that. I was scared…I thought about it all the time. I'm sorry it took me this long to face you."

"I don't think I could ever actually hate you, Jess. There were definitely times over the past year where I wished I had never met you and given you the chance to hurt me like you did…..But, I never actually hated you. I don't think I could ever really hate anyone that I cared about as much as I cared about you."

Jess smiled tentatively. "So, if you don't hate me." He eschewed charm for honesty, putting all he had into what he was saying, knowing it was do or die time. "And I certainly don't hate you….What do you think? Can we maybe be friends? At least…." He mentally kicked himself for adding the last part. He had no right to expect friendship from her, never mind anything more than that.

"I don't know, Jess." Rory cocked her head to one side with a sad little frown on her face. "I'm not sure how friendship would work for us. I honestly can't picture what that would look like at this point. And, I'm just really busy right now, with Yale, and the newspaper, and just everything…."

"Ok. I get it. That's fair." Jess nodded, averting his eyes past Rory, needing a moment to regroup.

Rory sighed. "Can just not hating each other be enough for now? With my mom dating Luke I'd like us to be able to be in the same room and get along. It's weird that they're avoiding each other this weekend because we're both home and they feel like they need to keep us apart. I don't want to live like that. And I don't want them to have to either. It feels so awkward and terrible."

"Yeah. It does." Jess paused. "Ok. We can start with just not hating each other. I'm good with that. Maybe someday we'll move up to co-existing in the same room at the same time. Then, maybe we'll become casual acquaintances. Then, who knows, maybe one day we'll be step-cousins." Jess smiled, and when Rory smiled back, he felt a comfortable warmth spreading through him from the inside. He couldn't keep dwelling on how he had let this girl go. There was only now. He held out his hand to solidify their deal, creating an opportunity for them to touch, at least in some small way. If she pulled him into a hug instead, all the better, but he knew it wasn't his place to initiate that kind of contact right now. "To not being enemies?"

She rolled her eyes gently and shook his hand, a small smile playing on her lips. "To being future step-cousins."

When Rory let go of his hand and took a step back, Jess knew he should take it as his cue to go. "All right, I'll see you around then, step-cuz."

Rory wrinkled her nose. "That sounds weird." Jess agreed, but he liked thinking it might resurface as a shared joke further down the road when Luke and Lorelai got married.

Jess nodded, as if considering. "You're right. I'll see you around then, Rory." He turned to go, his spirits lifted immeasurably.

"Hey Jess!" He turned back, trying not to get his hopes up. "My mom told me what you did for Dean. That was pretty great of you. I hope you know that." She paused, looked away for a moment, then straight back at him. "You're so much more than just the bad stuff you've done. I hope you know that, too."

Jess smiled, tilted his head in a small nod, and walked away.

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Dean didn't need to stand outside deliberating. He had started planning out what he was going to say as soon as he knew he was going to be in Stars Hollow. He knew he could be persuasive if he could just have a few minutes alone with her. He knew Jess would be pissed if he had any idea where he was right now, but he couldn't let that hold him back. He wouldn't feel right until he knew he had tried. He pushed through the door, holding it open with a smile for an older couple on their way out, then walked up to the reservation desk.

"Dean!" Lorelai came out from behind the desk smiling broadly and reached up to pull him into a hug. "It's so good to see you!"

"It's good to see you, too, Lorelai. Really good."

Lorelai released Dean and stepped back, looking up at him with a bright smile. "Luke told me that you were going to be in town, but I wasn't sure if we'd get a chance to meet up. I'm glad you came by. Let me go tell Michel that I have a guest and we can grab a cup of coffee in the dining room. How does that sound? Do you have time to sit and catch up for a bit?"

Dean nodded, smiling warmly at Lorelai, remembering the way she had welcomed him into her life and made him feel comfortable when he was dating Rory. "That sounds great. I would love to catch up with you. There's actually something I want to talk to you about."

"Really?" Her expression turned curious, an eyebrow shot up playfully. "I'm intrigued! All right, well let's get to it. Grab a seat in the dining room. I'm going to go get us coffees. Do you want lunch? Knowing Luke, he probably already fed you."

Dean laughed. "He did. The second we walked in the door."

Lorelai smirked. "Yeah, Luke's good like that."

"He is." Dean agreed with a warm smile.

"Then that works out well because you're just in time to have dessert with me! I know Luke didn't give you dessert!"

Dean followed Lorelai into the dining room and watched her walk into the kitchen. He headed to the table furthest away from the only other group of dining guests and sat down. He felt very optimistic about this. Lorelai was a good person, warm and caring. He was sure she would understand what he wanted to tell her. That he could get her to see Jess the way he did and convince her that he wasn't the same boy she remembered.

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Luke was sitting on the bench outside the diner reading the newspaper when Jess walked up, his mood much improved over the last time Luke had seen him. "Hey Luke." He smiled down at his uncle. "This is a good look on you, loafing around in the middle of the workday. You should do it more often." Jess plopped himself down on the bench next to Luke and leaned his head back, closing his eyes against the bright afternoon sunshine.

"It's Saturday. It's only a workday for people like me who spend too much of their time working."

"Is Dean inside?"

Luke folder the paper. "No, Dean went out a while ago." Luke idly rolled the newspaper into a tube and lightly knocked it on Jess' thigh a few times as he spoke. "I closed the diner to spend time with you guys and I turn around and everyone's gone."

Jess turned his head, resting it sideways on the back of the bench to look at Luke. "Sorry. I just had to get away for a bit. I'm all yours now until we get back on the bus tomorrow."

"Yeah? And what did you run off to go do, nephew?" Luke tensed slightly at the thought of Jess having sought out Rory, but from Jess' smile and relaxed posture, it didn't seem like it could have gone badly.

"Nothing bad. Don't assume the worst like that."

"Hey, I'm not assuming anything. Don't assume you know what I'm assuming." Luke smiled.

"I ended up reading on the bridge for old times' sake." Jess leaned forward enough to pull a paperback out of his back pocket as if to validate his story.

"Yeah. Is it the same as you remembered it?" Luke asked casually.

"Not much changes in Stars Hollow, does it?" Jess said, a non-answer if Luke ever heard one. Luke didn't respond. He didn't mention that the bridge was currently blocked off for construction after two of the boards had snapped last week. He would normally call Jess out on lying to him, but if he had gone off to see Rory, Luke wasn't sure if he wanted to know about it. It would only make him worry. Plus, Jess was an adult now. Maybe he deserved some privacy about this sort of thing. Luke knew he would hear about it from Lorelai soon enough if anything were to come of it, good or bad.

"Hey, Dean said you left through the back door."

"Yeah. I didn't want to walk through the diner again after the reception I got this morning. I was all Stars Hollowed out."

"There is no back door to the apartment, Jess. One of these days you're going to tell me how you get in and out without me seeing you walk through the diner-"

"Hey." Dean walked up to the bench. "What are you guys up to?"

"You're looking at it." Jess answered, slumped loose-limbed on the bench, a contented smile on his face. "Where did you go?"

"Oh, I just uh, went over to Doose's to talk to Taylor about maybe working for him again when I move back. And maybe renting an apartment in one of his buildings. He said he would give me a discount if I agreed to do some of the yardwork and maintenance stuff."

"That's great, Dean. But, make sure the discount is worth the work." Luke advised. "Don't let Taylor take advantage of you. Hey, did he write you your letter?"

"Uh, yeah. He did." Dean held up the manila envelope he was holding at his side. "He called me a respectful and upstanding young man in it and everything."

"Well, that you are, my friend. Remind me to give you mine and Lorelai's later. I have them upstairs."

"Yeah, ok. Thanks, Luke."

"You go anywhere else?" Luke asked. "I can't imagine anyone being able to tolerate Taylor for the whole time you were gone. At least, not without being paid for their time."

Jess looked up at Dean curiously.

"Oh, uh, I went by Lindsay's to say hi. To see how she was doing, and uh, make a plan for tomorrow to meet up after Clara gets out of her party."

Luke nodded. "Lindsay's. Right." Luke didn't mention that Lindsay had come by looking for Dean and Clara not fifteen minutes ago, having heard through the Stars Hollow grapevine that they were in town and staying with him. He wondered if he had made a mistake by warning the boys that Rory was in town this weekend. Maybe it would have been wiser to have said nothing and let them assume she was away at Yale. But, it looked like whatever was going to happen had already happened. All he could do now was enjoy having his nephew home, and hope for minimal fallout later. "Hey, I feel like going bowling or something. You guys want to go bowling?"


	17. Chapter 17 - Stars Hollow Part II

**Chapter 17 Notes:** This is a short chapter to check in with our characters before we head into the final chapter and to wrap up the weekend in Stars Hollow. Thanks to everyone reading and reviewing. I greatly appreciate all the reviews and feedback I have received for this story.

 **Disclaimer:** I own nothing except my own obsession with Gilmore Girls.

 **Trigger Warning:** Homelessness. Mentions of 'off camera' domestic violence, death and past child abuse.

Jess' last experience with bowling had ended with him getting spanked in public. He was hoping this time would go better. The first and last time he had bowled, he had been around eight years old and had gone with Liz and one of her boyfriends. Jess had been terrible at it. Liz and the boyfriend had had too much to drink, no one had given him any instruction or paid much attention to what he was doing, and Jess had gotten increasingly frustrated. When he had bowled yet another gutter ball, they had laughed and mocked him, and he had lost it, screaming at Liz that she never helped him, that she was a crappy mother who didn't care about him whenever her stupid boyfriend was around. He accidentally knocked Liz's beer bottle off the table, then ran for the door when the glass shattered on the wood floor and he realized the magnitude of what he had done. The next thing he knew, the boyfriend had caught up to him, cutting off his exit, and then a drunk Liz had him by the arm, screaming bloody murder and hitting him on the seat of his jeans over and over again. Jess remembered crying, feeling scared and humiliated, trapped by Liz's hold on his wrist, the only thing keeping him on his feet. He remembered another woman who had been there with her family yelling at Liz to stop beating her kid, Liz dropping Jess to the floor to get in the other woman's face, still screaming, as the boyfriend tried to hold her back, the guy working at the counter telling them to get the hell out before he called the cops, and being whisked out the bowling alley so quickly that he hadn't gotten the chance to change back into his sneakers. He had been stuck wearing stolen, ugly rental shoes for the next month, Liz refusing to replace his sneakers on principle after the way he had acted, until eventually a neighbor had taken pity on him and given him a pair that her son had outgrown.

He was logically anticipating a better outcome tonight, but he still had misgivings about doing it at all. He sat on a plastic chair at their assigned lane, tying his current pair of ugly rental shoes, watching Luke and Dean pick out their bowling balls, smiling and talking to each other as they hefted a few different sized balls to test out their weight. Dean had lit up like a little kid at Luke's suggestion of bowling. Of course, Dean would like bowling. It was such a normal, all-American family type of activity. Jess bet Dean's family had gone bowling a lot. Luke's, too. He knew he was in the minority for having had a mere hour's worth of bowling experience in his life. Stuff like this was always awkward for him. The things that everyone expected everyone else to just know how to do. The stuff that normal parents had taught their kids, but that no one had ever bothered to teach Jess. He didn't know how to ride a bike, or swim. And maybe he wasn't the only city kid who had missed out on those two activities growing up, but it didn't stop there. He had never really played any sports. He had played exactly half a season of soccer when he was small and Liz had dated a man who had coached his own son's team and put Jess on it, but he had had to quit before the season was over when they had broken up and Liz had claimed it was too painful for her to be around the guy, even just to drop Jess off for practice. Other than that, his only exposure to sports had come from gym class, which he often skipped to avoid embarrassment. He didn't think he was particularly uncoordinated, he had always been small but quick and agile, he just hadn't had a lot of opportunities to play sports when he was a kid, and the older he got, the more self-conscious he felt about his lack of athletic skill. When situations like this presented themselves, Jess usually came up with an excuse to opt out of the activity to avoid the humiliation of having people learn that he couldn't hit a three pointer or throw a tight spiral or knock down a sufficient number of bowling pins.

"Hey, Jess, come pick out your ball!" Luke called over to him with a grin on his face. Jess smiled back as he got up from his chair and headed over, knowing he was safe tonight. That he might be met with surprised looks when he told them that he had never really bowled before, that was natural, but he wouldn't need to feel embarrassed. They would understand and be happy to give him pointers. They cared about him and knew about his childhood and accepted him anyway. He thought about how good that felt. He thought about where he had been last summer, lost and depressed, feeling hopeless and alone as he rode a bus cross country. About how grateful he was to have reconnected with Luke, to have become friends with Dean, and to finally be out from under the huge weight he had been carrying around since he had run out on Rory. He was feeling good. Being a shitty bowler wasn't going to get him down. Not today. He had been dreading coming back to Stars Hollow, but today had turned out to be a really good day.

Jess approached the ball rack, an easy smile on his face. "All right, so I'm new at this whole bowling thing, but I watched a lot of Flintstones as a kid, so I think I'm in good shape here." Dean laughed and shook his head, while Luke smiled at his nephew, warm and indulgent. Jess picked up the ball closest to him and looked it over with an appraising eye. "What exactly am I looking for in a bowling ball, anyway? I'm guessing it's like picking a cantaloupe and I'm looking for a good color and a pleasant smell."

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The last time Dean had slept in a bed this comfortable had been at his aunt and uncle's house. Before he had messed up bigtime. He reflected on all the places he had laid his head since. The cheap and dirty motel room where he had panicked, unable to find work, as he watched his money run out, the cots in the homeless shelter where he had been too frightened to get any real rest. The night he had almost spent in a freezing alley, knowing there was a chance he might not wake up. Then, miraculously, Jess' floor. Where he had been warm and safe and fed and had access to a private shower. Where he had finally found respite from being alone and hopeless. Dean listened to the sounds of quiet snoring drifting over from the couch and Luke's room and he thought about how much better his life had become in just a few short months. He had a job and a roof over his head in New York, and solid prospects for another set for when he moved back to Stars Hollow. He had friends who cared enough about him to welcome him into their homes and their lives. He was on the verge of getting custody of his sister, and even though the idea of it terrified him, he still wanted it more than anything. And on days like today, being back in Stars Hollow with Luke and Jess, knowing he had good people in his corner, made it feel much less scary.

He thought about how well today had gone. He had been worried about having to lie to get away from Jess in order to go talk to Lorelai, but he hadn't needed to. Jess had snuck off on his own first, vague about his destination and plans. From the complete change in his mood when they had met up later, Dean suspected Jess had sought out Rory, and that things had gone well. Jess had seemed relaxed for the first time since arriving in Stars Hollow. And even though that made Dean happy, he knew it would hurt if he had to watch Jess and Rory get back together. But he meant what he had said on the bus. He wouldn't stand in Jess' way. Not after everything Jess had done for him. Jess deserved something good.

Dean thought about his own conversation with a Gilmore. He thought it had gone pretty well with Lorelai. She had tensed noticeably when he had first brought up Jess, but after going on about how kind and generous Jess had been to him in New York, taking him in, feeding him, being his friend, saving him in all the ways that really mattered, he thought he had made her reconsider her long held beliefs about Jess' character. He had even told her about the night he had come home drunk and turned angry and violent, and how Jess had still protected him from himself and not let him stumble out drunk in the middle of the night. Lorelai said she had heard that story already, but Dean got the impression she had thought it was an exaggeration when she heard it from Luke. He could tell from her expression, the sympathy in her eyes, that she believed his version. He had talked about how much Luke meant to Jess, how he was like the parent he never had, the good parent who really cared about him and wanted what was best for him. He told her that he knew that her relationship with Jess was stressful to Luke, and that he also knew it wasn't any of his business, but since he had first-hand knowledge of how much Jess had changed, and since he cared about all three of them and was grateful for everything they had done for him, he felt like he owed it to them to at least try to help fix things. Lorelai had told him that she appreciated his concern and him taking the time to come see her like this. She said he had definitely given her things to think about. And that was all he could do, really. The rest was up to her.

He thought about bowling with Jess and Luke. Bowling was one of those things that always put a smile on his face and made him feel like a happy little kid again. He thought about all the times his family had gone bowling over the years, and all the memories. His dad being playfully competitive with him as Dean had gotten older and his scores has improved. His mom entering in ridiculous nicknames for everyone on the scoreboard. The time they had teased Clara about for at least a year afterward when she had accidently dropped the ball on her backswing, startling herself and yelping like a frightened puppy at the loud, unexpected boom behind her. He thought about going on triple dates to the bowling alley with Lindsay and two other couples they were friends with in high school. How he had been surprised at how seriously Lindsay took it, and how much fun it had been competing with her. Tonight, it had felt like such a normal thing to do, almost like he was part of Luke and Jess' family.

He could tell Jess had been insecure about not being very good at it. It had made him think about what he knew about Jess' mom, and he wondered what else Jess had missed out on during his childhood. It made him feel good to know that Jess trusted him enough to do something badly in front of him. He didn't think exposing a vulnerability was something that came easy for Jess. Luke had shown Jess the basics and then offered up so many pointers every time it was Jess' turn that Jess had finally told him to back off and just let him bowl the damn ball. But, his words held no heat and he had been laughing in exasperation when he said it. Luke had stepped back, his hands up in surrender, smile on his face as he apologized for getting carried away. As they sat watching Jess concentrate on his approach, Luke told Dean that he had always wanted to bond with Jess by teaching him a sport, but he figured he had missed out on those years and he had gotten a little too excited when he finally got his chance tonight. Dean had smiled at that, even as he had felt a twinge of pain at the memories it evoked of his dad teaching him to shoot a basketball when he was little or all the games of Horse and Around the World they had played in their backyard in Chicago. He couldn't have that anymore, but he was starting to get to a place where he could be grateful he had had it. And he could have this. It was something. Jess hadn't broken a hundred the whole night, but Dean knew he had had let himself have fun anyway. And that meant a lot to Dean.

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Luke was hot and annoyed, working the grill during the Sunday morning breakfast rush when he would rather have been spending time with Jess before the boy had to head back to the city. Caesar was out sick again. Had Luke known this _before_ he had opened the diner, he wouldn't have. But, by the time Caesar had called to say he wasn't going to make his shift, Luke already had a diner full of customers and no one to relieve him at the grill. He had sucked it up and remained in the kitchen, knowing the rush would die down shortly, leaving him free for a while before Jess and Dean had to catch their bus. Dean was going to go pick up Clara in a little while and take her to see Lindsay, and as much as Luke liked having Dean around, he was looking forward to some one on one time with his nephew, too.

Luke heard Lane squeal and he peeked into the dining room over the shelf where he placed orders for pickup. He knew that squeal. Sure enough, he saw Rory and Lane hugging and bouncing up and down by the door, Lorelai barely in the door, watching them with a smile. His eyes went to Jess and Dean, sitting at a four-top and looking toward the commotion, both angled away from the kitchen. Luke wished he could see their faces. He wasn't sure what to make of this. Lorelai had been the one to suggest they each do their own thing this weekend, none too subtly implying her intent to keep the kids apart. Surely, she would know he would be giving Jess and Dean breakfast at the diner this morning and that there would be a high likelihood of running into them if she and Rory came in. Luke wondered if this meant she had had a change of heart. Luke plated the French toast he was finishing and set the plate on the shelf, hitting the bell to alert Lane to an order. He saw Lane look toward the kitchen at the sound, say something he couldn't make out to Rory and walk toward him to pick up the order. "Hey Luke, Rory's here!"

Luke nodded. "I see that. Thanks."

Lane frowned slightly at his tone as she put up two new orders and picked up the French toast and Luke realized the situation had him more stressed than he thought. He threw bacon onto the grill and poured out circles of pancake batter to start the new orders. He really wanted to get out there. He was going to need to start training Lane on the grill for just such emergencies.

When Luke peeked out into the dining room a few seconds later, he saw Lorelai and Rory standing at Jess and Dean's table, both boys on their feet to greet them. Jess' posture seemed less tense and not as defensive as the last time Luke had seen him around Lorelai when they had had lunch together in New York. But, he supposed that was due to Rory's presence this time. Luke watched as Lorelai greeted the boys with a broad smile and words he couldn't hear, then stepped in to pull Dean into a quick hug before moving past him to do the same to Jess. Luke could tell from Jess' stiff movements that he had been caught off guard, but he let himself be pulled into the briefest of hugs, even raising one arm to half-encircle Lorelai for a split second in return. Luke heard a loud hissing and looked down at the grill, sighing as he flipped over the bacon.

Rory had greeted both boys with a smile, a few words and a small wave. She had started talking to Dean while Lorelai had hugged Jess. Luke made note of her playing with her hair as she faced Dean, listening to something he was saying. He also noticed that Dean hadn't gone in for a hug with Rory, which seemed unusual for Dean, but maybe that would have been too awkward with an ex-girlfriend. Lorelai was the first to pull out a chair and then all four of them were seated at the table. Lorelai was talking across the table to Jess. She was facing the kitchen and Luke saw that she was being genuine. This was her real smile. Not the closed off 'tolerating Jess for Luke's sake' smile that she normally wore around his nephew.

Lorelai laughed at something Jess said and looked toward the kitchen, leading Luke to believe Jess had made a joke at his expense. He didn't care. Whatever got them laughing together. Her eyes locked on his and Lorelai said something to the table in general and stood up. Luke slapped everything onto plates as quickly as he could and set them out for Lane. If Kirk's bacon wasn't as well done as he liked it, oh well, he could deal with it for one day. Luke would consider it payback for Kirk asking Jess if he had been sleeping in an actual gutter yesterday. Luke walked out from the kitchen and stood behind the counter, a smile forming on his face. "Hey Lorelai." He leaned across the counter for a quick kiss. "I didn't think I'd see you guys this morning."

Lorelai scrunched up her face. "Yeah, about that. Rory and I decided it was weird for the two of us to avoid each other just because she and Jess are both in town. It didn't feel right."

"Is that so?" Luke could feel the smile taking over his face. "And what brought on this change in philosophy?"

"Well, Rory and I had a couple of interesting conversations yesterday. Then we talked things over just the two of us last night and we came to the conclusion that if you and me are dating, then our families are dating, too."

"What?" Luke shot a nervous glance over to the kids' table, not sure what he was looking for, but what he saw seemed harmless enough. Dean leaning back in his chair, his arm slung casually across the back of Jess', Rory dividing her attention between Jess and Dean as she spoke, Jess leaning intently forward on the table and nodding.

Lorelai laughed. "I don't mean literally dating. Relax. I just mean that I need to spend more time with your family, get to know Jess better."

"Oh, yeah?" Luke was surprised but pleased, the grin back on his face.

"Yeah. I feel like things are going really good with us. Don't you think?"

Luke nodded. "I do. I very much do think." He wasn't sure how much sense he was making, but he was too excited to care.

Lorelai returned the smile. "So, I'm starting to think this could be for real. You and me. And if that's the case, it won't just be you and me. It will be all four of us. You. Me. Rory. Jess. Our own tiny little Brady Bunch, but with better hair. And I want that to work. Because if that doesn't work, this." She waved one hand back and forth between them. "You and me, won't work either. No matter how much we want it to. And I really, really want you and me to work."

"Me too. I want you and me to work, too."

"And you're already in a good place with Rory." Her smile became a smirk. "I mean, you two are always chatting it up about your common passion for Yale architecture. I can barely get a word in edgewise. It's all vaulted archway this and flying buttress that, with you two!"

Luke laughed at Lorelai's reference. "Hey, mock all you want-"

Lorelai's expression went serious. "I'm not mocking. You have a history with her. You care about her and she cares about you. She trusts you to be good to her. And, so do I. How much you care for Rory is one of the things I love most about you." Lorelai paused for a moment. "And, I think maybe I need to catch up in that department. How things are between me and Jess can't make you feel very good about you and me."

"Well, uh." Luke stumbled, not sure how to respond, not wanting to dampen this moment. "I get that you two have your issues, and everything. I know it's not easy for him. Or for you."

"It hasn't been easy. But, I think I can do better. Me and Jess may never be as good as you and Rory, but I think we can be better than we are right now. I want us to be. Because I love you so much. I love you and me so much. And I don't want this to come between us. I don't want anything at all to come between us. I want this to work."

"I love you so much, Lorelai." Luke felt his voice catch. He leaned across the table and pulled Lorelai into a real kiss, gently cupping the side of her head with his palm. All the detail he was never able to see before, about their future together, about Lorelai and Jess, was now so clear in his mind. He could see comfortable family dinners when both kids were in town. Jess recommending a novel he was reading to Lorelai. Lorelai forcing a beloved but obscure eighties movie on Jess. Jess pretending to let Lorelai force junk food on him. Jess asking Lorelai's advice on something to do with a new girl. Lorelai and Jess greeting each other with real hugs when they visit the boy in New York. Lorelai tearing up at Jess' wedding and being a playful and caring almost-grandmother to his children. Lorelai as part of the safe and loving family Luke had always wanted to give his nephew.

There was nothing holding him back now. Luke was all in.


	18. Chapter 18 - Big Steps Forward

**Chapter 18 Notes:** Oops, it looks like I was wrong about the last chapter being the second to last one! This one is now the second to last one. There were a few more things I wanted to add before I wrap up. The final chapter may take a little longer to get posted. I just started my first semester of grad school and between school and work, it's been harder to find time to write. Thanks again to all the readers and reviewers out there. I really appreciate all the comments that you guys have so generously left me.

 **Disclaimer:** I own nothing except my own obsession with Gilmore Girls.

 **Trigger Warning:** Homelessness. Mentions of 'off camera' domestic violence, death and past child abuse.

Dean waited until Clara was asleep. He knew she would fall asleep quickly. She never got enough sleep when she and Sabrina had sleepovers and she was always tired and cranky the next day. He knew the bus would put her out. He was glad she had fallen asleep leaning against the window instead of his shoulder. He turned in his seat to face Jess, who was sitting alone across the aisle, reading a paperback with his discman earphones in his ears. Dean could never understand how he could read and listen to music at the same time.

"Hey, Jess." Dean whispered, trying not to wake Clara. When he got no response, he poked Jess in the arm.

Jess looked up, frowning at the intrusion, pulling an earphone off one ear. "What?" He asked at normal volume.

"Shhhh! Be quiet. Clara's asleep." Dean admonished in a whisper. "Can we talk?"

Jess rolled his eyes and pulled off his other earphone, closing his book but keeping a finger inside to hold his page. "And what exactly do you want to talk about in this super-secret whisper conversation?" Jess whispered back, hoping Dean would get the picture of how ridiculous this was.

It was Dean's turn to look annoyed. He stood up. "You're right." Dean whispered back, pushing on Jess' shoulder. "This is silly. Move over and I'll sit with you, so we can talk."

"Jeez, Dean." Jess gave in to Dean's pushing and moved into the window seat. He watched Dean take the aisle seat next to him. "All right. Talk fast so I can get back to my book." In truth, Jess had stopped reading a little while ago, his mind replaying their breakfast with Lorelai and Rory and going over every detail in his head. And he wanted to get back to doing it in peace.

Dean looked pensive, but unsure of how to start. Jess figured he knew what this was about. Now that Dean was in his physical space, Jess felt they were too close to face each other comfortably. Instead he settled his gaze on the seatback in front of Dean, where he could avoid direct eye contact, but still watch Dean from the side of his eye. "Well? Is this about Rory?"

Dean nodded, looking a little relieved to not have to start the conversation. "Yeah. I, uh, I just wanted to check in with you about what happened with her. You went to see her yesterday, didn't you?"

Jess sighed. "Not that it's any of your business, but yeah, I did." Jess glanced to his left and took in the flash of hurt that crossed Dean's face.

"You're right, it's none of my business." Dean looked down at his lap. "I'm sorry. I just wanted to see how it went. And make sure everything is ok with you and me." He looked up at Jess like a kicked puppy, and Jess sighed again, feeling like an ass for not being more cognizant of how much more painful this entire trip had to have been for Dean.

"Of course, everything's ok with you and me." Jess looked at Dean and tried to smile reassuringly. "Why wouldn't it be?"

"I don't know. Just checking, I guess. We don't have a very good track record of getting along around Rory. It went ok when you talked to her, though, right?"

"Yeah. I mean, she accepted my apology and everything. She kind of shot down my offer to be friends, but I guess I can understand that."

"She seemed pretty friendly at breakfast."

"Yeah, I wasn't expecting them to come by like that." Jess paused. "She said she doesn't hate me anymore, but, I don't know…..I get the impression this morning was more about not wanting things to be weird for her mom and Luke. Plus, she definitely wanted to see you. She seemed pretty interested in how you and Clara were doing." Jess shrugged. "I don't think anything is going to happen with us, if that's what you want to know."

"But, you'd like it to. I mean, you're still into her, right?"

"I don't know. Maybe." Jess felt uncomfortable admitting his feelings, but he didn't want to lie, either. "Yeah, probably." Was the best he could do. "I'm not sure what I want matters anymore, though."

"Why not?" Jess looked away from Dean's scrutinizing gaze, feeling too exposed, and wanting to go back to his book and hide. He had felt positive after his talk with Rory yesterday. He had thought he had done a better job of getting over her, that he had really wanted to just get his apology off his chest and make things right with her, but seeing Rory again had brought back so much feeling for Jess. Even in their short conversation in front of the bookstore, he had felt an intense connection. He had convinced himself that she had to have felt it, too. But today at breakfast had felt pleasant but superficial. Lorelai had been more interested in asking about Jess' life in New York than Rory, who had focused more on Dean and Clara's situation when she wasn't talking about Yale. He knew he had let his expectations get too high based on one very short conversation the previous day. All she had really agreed to was not hating each other and not making things awkward for Luke and Lorelai. He had thought she was just saying that, but after breakfast today, he was starting to believe she may have actually meant it. He knew he needed to let that be enough. He was only going to torture himself if he couldn't.

"I don't know. I think I really hurt her when I left. I don't think she trusts me anymore. And, anyway, she's busy doing her Yale thing right now. Living her ivy-covered dream, and all that crap. Me and her wouldn't make any sense right now."

Dean nodded, taking this in. "Yeah. I guess."

"Would you really be ok with us getting back together anyway?" Jess was genuinely curious. He would most definitely not be ok with Dean and Rory getting back together, but he thought Dean had a more generous nature than he did.

"I think so. It would probably be hard to watch you guys together at first. Just like it was the first time around. But, I'd live through it, like I did then. And I'd be happy for you if it's what you wanted. Both of you."

Jess was skeptical. "Do you honestly not have feelings for her anymore?"

Dean shook his head, his expression serious. "That's not what I'm saying. I do have feelings for her. She was the first girl I ever loved. I'll probably always have feelings for her." A goofy grin spread across Dean's face. "But, right now, I guess my feelings for you are stronger."

Jess rolled his eyes. "Jeez, and you tell me I'm ridiculous."

"I'm serious. At this point, being friends with you means more to me than the chance to get back together with Rory."

"I'm touched." Jess' said, sounding more sarcastic than touched. "How 'bout you take your feelings and go back to your own seat now?"

Dean ignored him. "I mean, there are so many things about Rory that I still love, for sure. I mean, you get that, she's a great person. But I'm not so sure we were as good together as I thought we were." Dean paused. "There was some not so good stuff that I hadn't really thought about in a long time. I feel like after we broke up, I had this idealized version of her in my head. But, when I saw her again today, a lot of the old stuff came back up for me, and now it's hard to remember the good stuff without the not so good stuff"….Dean trailed off.

"What do you mean? What kind of stuff?" Jess was interested. Rory had always made it sound like Dean was the perfect boyfriend. He hadn't thought they had had any not so good stuff.

"I mean, like, when I told her I loved her and she said 'thank you.'"

Jess laughed. "Ouch. But, hey at least you told her while you guys were actually dating." Jess reflected on the fact that he had never told Rory that he loved her in the present tense. Even yesterday he had only been able to admit to his past feelings. He thought about how Dean was much braver than he was.

Dean breathed out a quiet laugh. "Yeah. And she did say it back eventually. So that's something. But, like, I built that car for her with my dad, right? That was so much work. It took us a really long time. And I was so proud of it when I gave it her. And then she let a guy I hated, who was always a total dick to me, drive it and wreck it. No offense."

"None taken. It really was an accident."

"I know that, but that didn't feel like the point. And I made her this bracelet in shop class and gave it to her for her birthday, and I guess she lost it once and never told me. I overheard Babette and Miss Patty saying that Rory was running around town looking everywhere for it."

Jess stayed silent, telling himself he had only played a role after the fact in that situation. Dean was right, Rory had lost the bracelet on her own. Dean probably didn't even realize how long it had taken her to notice it was gone, either.

"And now looking back, I think it was probably my fault. Maybe I was too into her and I did too much. She never put as much time or effort into doings things for me. Do you know she never even came to one of my hockey games the whole time we dated? Then after we break up, she shows up at a game with Lane. Like all of a sudden she's into hockey or something."

Jess remembered meeting Rory after that hockey game. He knew she had only gone to the game to prove a point to him that she wasn't going to wait around for him to call, but he wasn't sure if it would do more damage than good to tell Dean that. "I'm sorry. That sucks."

"Yeah, it did suck. I mean, I learned to ballroom dance and went to a debutante ball for her. In a top hat and tails and white gloves." Jess couldn't help laughing at that image. "Yeah." Dean agreed. "It is pretty funny. How many guys would do that in high school? But, she never bothered to come to one of my games." Dean laughed. "It's all so ridiculous when I think about it now."

"Huh." Jess said for lack of anything better. In high school he had thought Dean wasn't smart enough for Rory, that she was the one who was settling, but he had never thought about their relationship from Dean's point of view.

"I mean, don't get me wrong, we were good a lot of the time, really, but things were always uneven between us. I knew I was more into her than she was into me. But, I figured every relationship is a little unequal, right? Like no two people can ever love each other exactly the same amount. But then, everything got worse between us when you got to town. She was into you right away. I could tell I was losing her, and I got pretty needy, which I'm sure annoyed her. And she started treating me pretty bad. And I spent way too much time putting up with it, just happy to be with her at all. Like that time she told me that she wanted to stay home alone, and then I stop by anyway to surprise her with ice cream and you're there, just hanging out eating dinner with her and Paris. And how jealous she got when you started dating Shane. I saw her giving Shane this really dirty look one time at the diner and I didn't get it because Rory was never like that. I didn't think she even knew Shane. Then you walked out of the back and kissed Shane, and I got it. It was all so obvious. And that whole thing at the dance marathon. She treated me like garbage that night. I spent hours there watching her in that contest, fetching her and her mom water and coffee when they couldn't leave the floor, filling in for Lorelai when her heel broke, and all she cared about was what you were doing with Shane. I remember talking to my Dad after I broke up with her that night. He told me that I'll know a relationship is right when I don't feel like I'm constantly chasing the girl. And I felt that way with Rory from the second you rolled into town. Maybe even before. So, yeah, I'll always have feelings for her. Maybe I'll always still kind of love her…but I don't think she was very good for me…And then I think about Lindsay, who was so great to me when we dated. Who was there for me when everything happened with my parents." Dean's voice caught slightly, and he paused to get his emotions under control. "Who is still so great to Clara, despite how things ended between us. But, she was always more into me than I was into her. I was never really over Rory the whole time I was with her." Dean shrugged. "I don't know. I guess it's just hard to find something where things are equal, you know?"

Jess nodded, wondering if Rory thought of him the way Dean thought of her, as someone she would always have feelings for, but who wasn't good for her on a basic level. It wouldn't be a completely unjustified opinion. Maybe he was the only one stuck in the past. "I'm sorry things were so bad for you once I got to Stars Hollow." Jess kept his eyes straight ahead, avoiding Dean's. "If I had known you then like I do now, I never would have worked so hard to steal Rory from you. I've never felt about anyone else the way I did about her." Jess noted his automatic use of the past tense. "I guess I acted pretty shitty because of it. And I'm sorry."

Dean shrugged. "It's ok, Jess. You were kind of a jerk about it, but you were looking out for yourself and what you wanted. So was Rory. I get it. I mean, you couldn't have stolen her if she wasn't willing to be stolen, right? She wasn't happy with me by then, and she thought things would be better with you. Our time was just up. My time with Rory was up as soon as she met you." Dean grinned then. "And, not to be super lame or anything, but me and you, our time is just beginning. I think we're going to be friends for a long time. Maybe the rest of our lives. And I don't want anything that might happen between you and Rory to get in the way of our friendship. I will absolutely not allow that."

"Jeez, you really think that's not being super lame? You might want to work on that."

Dean laughed softly. "I'm serious, Jess. I know you hate when I say stuff like this, but I'm so glad I met you, despite all of our high school shit. I'm so glad we connected in New York and became friends. I'm so grateful that you took a chance on bringing me home with you that night. That you've let me into your life like this. You've done more for me than anyone other than my parents ever has. I will never forget any of it. And I will always be your friend."

Jess couldn't look at Dean. He felt a little choked up. He couldn't deal with stuff like this, earnest and open emotion. Especially not sitting in the window seat on a moving bus with no way to escape, nowhere to look that felt safe. He nodded once, facing straight ahead, hoping Dean would take the hint and move on.

Jess could tell Dean was grinning now, could hear it in his voice. "It's like Kirk said, you found me sleeping in a gutter and you rescued me. No matter what happens with us in the future, I will always love you for that, man."

Jess nodded again, eyes burning into his lap, feeling himself shutting down. He wanted to make a sarcastic comment about Kirk actually saying the exact opposite, but he didn't trust himself to speak. He felt himself being pulled gently toward Dean, long arms wrapping around his shoulders. He lifted one hand tentatively to Dean's side, not wanting to reject the gesture, but never quite sure what to do with his hands during a hug. When he pulled back a moment later, Dean released him without resistance. Jess sniffled once and glanced at Dean for a second before refocusing straight ahead. He tried to infuse sarcasm into his voice but could tell he was falling short of selling it even as he spoke. "So, you think it's time to go back to your own seat now, or what?"

Dean snorted and laughed. "You want to know what I think? I think you're an ass, that's what I think." Dean slapped Jess on the thigh good naturedly and started to stand up.

Jess already regretted what he had said, his attempt to hide behind prickly sarcasm. He didn't want to be like this anymore. He didn't want to feel like a coward all the time. "Hey Dean." He looked up at Dean, who had paused midrise to look back at him. "I'm glad we're friends, too. Really. And I'm sorry if I'm not as good at this as you are." Dean smiled warmly at Jess, gave his shoulder an affectionate pat and moved back to his seat beside Clara. Jess stayed in the window seat and turned his attention to the passing scenery, a small smile reflecting back at him in the window. As awkward as their exchange had been, Jess felt better for it. He thought maybe he could count Dean as a person in his life now. Somewhere below Luke but above Liz.

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"Really? He's not contesting it? Like, not at all?" Dean was sitting in Nicole's office, relieved to have just learned that his uncle wasn't going to make things difficult for him and contest his petition for custody of Clara, as he had expected him to.

Nicole nodded her head, a warm smile on her face. "That's right. Raina said she had a very productive meeting with Mel and she was able to make him see that it was better for everyone if he didn't contest the petition. Just between you and me, Raina threatened to make your sister's allegations of domestic violence public if he caused any trouble. Also, between you and me, I think she really enjoyed doing it. She came back to the office with a big smile on her face and took me out for a drink to celebrate."

"Wow. I can't believe that got him to back down so easily." Dean's first reaction, before he had time to censor his thinking, was how fortunate it was that his uncle had hit his aunt. Then he pictured Gretchen with a cast on her wrist and he felt like an asshole for the thought.

"All it takes are allegations, the right allegations, to ruin a career. Mel knows that." The pleased smile on Nicole's face made Dean wonder what exactly his uncle had done to make enemies of Nicole and Raina, but he figured it would be inappropriate to ask.

"So, what happens next?" Dean thought about all they had done so far. The background checks, the meetings with the social worker, his and Clara's letters to the judge, his character references, his meeting with Nicole and Raina. He was excited that he was finally in the homestretch. Scared, but excited.

"Well, all your paperwork has been submitted to the judge. We should be notified of a court date soon. You keep your job in the mailroom, see your sister every week and stay out of trouble and we shouldn't have a problem. I see no reason why you won't be awarded custody when we get in front of the judge."

Dean nodded, taking it in. "That sounds great. Thank you, Nicole. Thank you so much for all your help."

"It's been my pleasure, Dean, really. I usually practice business law, and I don't get the chance to really help someone on a personal level like this very often." Nicole smiled warmly at him. "So, how did things go on your trip to Stars Hollow? Were you able to talk to people about apartments or jobs? The judge will grant you a certain number of days to produce a lease of where you and Clara will live and show proof of income, but it won't be a very long time, so it's definitely good for you to get a jump on that now."

"I did. I, uh, I talked to Taylor when I was home and he said that he's expecting to lose a few employees at the start of the summer and that he would be willing to hire me, either back at Doose's or at the ice cream shop." Dean huffed out a small laugh. "Though, I'm not crazy about the uniforms he makes them wear at the ice cream shop so I'm really hoping something opens up at Doose's."

"You're willing to work for Taylor again. You must be made of some pretty tough stuff." Nicole smiled.

Dean laughed. "He gets a bad rap, but he's actually a really nice guy when you get to know him. I mean he's super fussy and everything, but once he likes you, he looks out for you. Like, he also said that I could kind of assist him with events and stuff sometimes, like with setting up for town meetings, stuff like that. And he has a few tenants who are moving out next month, so he said he might have an opening in one of his apartments. He went over the prices with me, though, and I don't think I'll be able to afford a two-bedroom. I might have to get a one-bedroom, give Clara the room while I sleep on the couch or something. Luke said he would give me some shifts at the diner if I needed it to make ends meet, too." Dean paused. "But, I got the impression that he would be doing it more to help me than because he needs the extra help. So, I think I would only take him up on that if I was really desperate. Otherwise, I would feel like I was taking advantage of him."

"Hmm, that sounds like Luke. I'm glad you have him in your life. He's a good person. And that all sounds very promising, Dean." Nicole hesitated. "Can I give you some unsolicited advice?"

"Uh, sure. Of course, you can, Nicole."

"There's nothing wrong with piecing together work like that. I did the same thing all through undergrad. But, Clara's only twelve. You'll have six years as her guardian before she heads off to college. Don't forget to plan for your own future in that time, too. Give some thought to what you would like to do as a career and take steps toward that goal. It may not seem like it, but even small steps matter. Look into taking a class or two when you can afford it. Look into scholarships if you can't. It probably isn't my place to say this, but you're a good kid, Dean, and a hard worker. And I know you'll work very hard to take care of your sister. Just don't forget to take care of yourself as well. Ok?"

Dean nodded once, embarrassed by how emotional he suddenly felt. "Ok. Thanks, Nicole."

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Jess read the email for the tenth time. He hadn't been expecting this. Deep down he was expecting either no reply or something along the lines of thanks but no thanks. Maybe even a reference to his manuscript being unreadable garbage, the likes of which they never wanted to darken their inbox again. Not an invitation to set up a call to discuss his book. Book. That was the word the publishers used in the email. They thought it could be a book. They were interested in talking with him and possibly working with him to help turn what he had sent them into something they wanted to publish.

He knew he should be excited. This had been the goal when he had sent them his manuscript. And he should be relieved that the first publisher he had hit up was interested enough to want to talk to him. But, all he felt was a nervous, sick feeling in the pit of his stomach. He had envisioned a yes or no response, which had probably been unrealistic. He hadn't thought about having to discuss, or possibly even defend, his writing. He thought about all the harsh criticisms he had leveled at books he had read over the years, sometimes even about books he mostly liked. He wasn't sure if he could handle that kind of criticism aimed at his own book, even by people who liked it enough to consider publishing it. It's not that he thought his book, he still couldn't get used to thinking of it as a potential book, was perfect. Far from it. But, it was intensely personal, and he was never good at discussing personal things.

He was thinking about how to respond and what the best time would be to set up the call when his phone rang. He glanced down at the small screen lying on the floor next to him. Not that there was any point. Only one person ever called him. It would probably stay that way until Dean was able to afford a cell phone. As he reached for the phone, he briefly contemplated sharing his news with Luke, but decided he would feel safer waiting until the book was actually published. He figured a lot could still go wrong at this point.

"Hey, Luke."

"Hey, Jess! How are you doing?" Luke's voice sounded off to Jess, overly excited, and maybe a little nervous.

"What's going on? Why do you sound weird?"

Luke chuckled. "Thanks, Jess. It's good to hear from you, too."

"Sorry." Jess shut his laptop so he could concentrate on talking to his uncle. "I'm good, Luke. How are you doing?"

"I'm good, too, nephew. Very good, as a matter of fact. See how nice and pleasant that was?"

"I do. Now, will you please tell me what's going on?"

Jess heard Luke sigh. "I do have something I want to talk to you about."

"Ok. What's up?"

"Well, I know Dean's really close to getting custody of his sister, now. I mean, according to Nicole, going in front of the judge is only a formality at this point-"

"You talked to Nicole?"

"Oh, uh, yeah, she was at the ice cream shop with Taylor the other day, for business, because she's his lawyer and everything…..so I went in to thank her for everything she's done for Dean, and she told me basically what you told me the other day, that it's probably going to happen really soon. So, uh, I was thinking about how Dean's planning on working for Taylor and renting one of Taylor's apartments, and I just got to thinking. I mean, no one should let Taylor have that much control over their life, right?"

Jess felt his stomach clench but tried to keep his tone light. "Hey, you're preaching to the choir on that one. I've tried telling him the very same thing."

"Right! I knew you'd agree with me. So, I wanted to do something to help him out…..but, I wanted to talk it over with you first. Make sure it was ok with you."

"Are you going to offer him a job at the diner?" Jess could already tell that wasn't Luke's plan. He knew what was coming and he felt himself shutting down, his voice going flat, his body feeling rigid with tension.

"Oh, uh, no. I mean, I told him I could give him some shifts if he needed extra money, to help him out you know, but I don't really need another full-time server…..Although maybe I could train him to cover the grill for days when Caesar's off….." Luke's voice trailed off in thought, and Jess knew he would have to refocus the conversation in order to get it over with.

"So, you called to make sure it was ok with me to train Dean as a back up cook at the diner?" Jess spoke slowly, drawing the sentence out.

Luke laughed. "No, uh, I was pretty sure you'd be ok with that part. I uh…..well, remember when you guys came to town a while back?"

"Yes, Luke. I remember. It was only a few weeks ago."

"Well, remember how different Lorelai was to you at breakfast the day you guys left? And how good you guys were getting along?"

"Can we please just cut to chase here?" Jess hadn't meant it to come out as that much of a snap. He sighed. "Just tell me what you want to say, ok?"

"Ok, Jess. Sorry. I guess I'm kind of rambling a little…."

"Yeah, just a little."

"Ok, well, things have been really good with me and Lorelai since you guys visited. Now that she's gotten over her issues with you and is more open to getting to know you, it's like this weight has been lifted and our relationship is better than ever. I mean, things are going really well, Jess."

"Uh-huh."

"And, I guess, we've been talking about this for a while, but now it just really seems right. And, I mean, it might sound quick, but we've known each other for so long…." Jess listened to Luke take a deep breath, feeling a bit like an ass that the person he loved most was so nervous about his reaction to sharing something this important with him. He figured the least he could do was not drag it out. He didn't like hearing Luke like this.

"So, you and Lorelai are moving in together and you want to know if I'm ok with you offering the apartment to Dean and Clara?"

Jess listened to Luke exhale a long breath, but this time it sounded more like relief. "Yeah, that's….that's it, Jess. I guess I'm pretty transparent, huh?"

"Well, I certainly wouldn't quit my day job to start a career as a secret agent if I were you." Jess listened to Luke's warm laughter and felt his own tension starting to ease, feeling like he was coming back to himself. "But, it's only because I know you so well."

"So, are you?" Luke asked tentatively. "Ok with it, I mean?"

Jess knew that what Luke was really asking had very little to do with the apartment. "They're going to need doors, you know."

"I know. They'll need privacy. If Dean's interested, I'll get Tom in there to close off the two bedrooms before they move in."

"Oh, I see how it is!" Jess felt a smile forming on his face. "I got all the privacy of living in an airplane hangar, but Dean and Clara get their own rooms, huh?"

"Clara's almost a teenage girl. It would be weird if they didn't have their own rooms."

"Hey, I _was_ a teenage boy, if you remember! And, that didn't rate _me_ a door."

Luke laughed softly. "Hey, nephew, I bought a whole building for you. Doesn't that count for anything?"

Jess thought back to how impressed Dean had been with Luke's generosity and what he had been willing to do to make space for Jess. "I suppose it counts for something. But, you have to admit, it was an odd choice to have Tom do that whole renovation and not turn the bedrooms into, oh, I don't know, actual rooms."

Luke was quiet for a moment. "Yeah, it was an odd choice." Luke paused. "You had just gotten here and everything. I didn't know you that well yet. You would barely talk to me or even stay in the same room with me for more than a few minutes….."

"What does any of that have to do with me not getting a door?" Jess asked, genuinely puzzled. "I hadn't earned it yet or something?"

"What? No! It's just…I think I was afraid that if you had a real room that you could go to that you'd lock yourself in there all the time and I'd never see you and we'd never get to know each other."

"Huh." Jess processed what Luke said. He had always assumed that Luke hadn't wanted to compromise the open plan of the apartment. But, he had never asked, because Luke was right, Jess hadn't spoken to his uncle much in those days.

"And, uh….."

"Oh, jeez, there's more?"

"Just that the week after you moved in, I was in the waiting room at the dentist and they had the TV on, and it was set to this talk show, and these parents were talking about having to take their son's door off the hinges so that he couldn't hide drugs and stuff in his room. And the kid reminded me of you, just all attitude and dirty looks and refusing to tell his parents anything about his life or what he was doing. And his parents just seemed so worried and scared. And I think that freaked me out and got stuck in my head, and, I don't know. It's stupid."

"Yup. Not going to argue with you there. That's pretty stupid."

Luke chuckled. "Gee, thanks, Jess."

Jess smirked. "Hey, if I don't call 'em like I see 'em, would you ever really be able to trust me?"

"It was stupid. I know it was. You were a really good kid, Jess. I should have given you a door."

Jess laughed. "I really wasn't. But, I appreciate that you like me enough to look back on me that unrealistically. But, wait." Jess feigned confusion. "Why didn't you put a door on your room? Was that so I could search your room for drugs, too? In case I ran out of my own stash. That was very considerate of you."

Luke laughed softly. "It didn't seem right to give myself a door and not give you one."

"Wow, your thought process is pretty scary sometimes! I'm glad it's not a genetic condition."

Luke chuckled quietly. "So, uh, you're ok with everything, right? I mean, I'll tell Dean that there's a stipulation that you get to stay over there if you want to whenever you're in town. Of course, you're welcome to stay with me and Lorelai, but if for some reason, you didn't want to, I don't want you to feel like you don't have a place to stay….so, are you ok with it?"

Jess thought it over, unsure whether this put him one step closer to gaining Lorelai as an almost-step-mother type person in his life, or to losing Luke as his almost-dad. Lorelai was young enough that they could still have a child of their own. And Jess didn't know where that would leave him. All he knew for sure right now was that Luke really wanted this, and he wanted Jess to want it for him. And Jess loved him. He had to trust that his relationship with Luke was strong enough that everything would work out all right. "I'm more than ok with it, Luke. I'm happy for you." And to Jess' surprise, he realized he kind of even meant it.


	19. Chapter 19 - Endings Are Still Hard

**Chapter 19 Notes:** Here's the final chapter. It's a bit of a long one. If you feel like leaving a review, I would love to hear what you think. Thanks to all of you who have taken the time to read this story and leave me reviews. I really appreciate every word you've given me. :)

 **Disclaimer:** I own nothing except my own obsession with Gilmore Girls.

 **Trigger Warning:** Past homelessness. Mentions of 'off camera' domestic violence, death and past child abuse.

All of a sudden, things seem to move very quickly. Too quickly for Jess' liking. Dean gets his court date. Jess watches Dean stand in front of a judge, nervous and fidgeting, as he promises to take care of his sister, and grinning broadly when he is awarded custody. His aunt is at the hearing, without her husband, and she takes them all out for a late lunch afterward. She's a nice woman who obviously loves Clara very much, and Jess feels bad for her, married to a shitty guy and now losing her niece. She puts on a brave face about wanting whatever Dean and Clara want and promises to come out to visit them in Stars Hollow often. They say goodbye to Gretchen and Clara outside the restaurant. Clara stays with her aunt and uncle until school ends in three weeks. Everyone agrees it wouldn't make sense to do anything else.

Jess watches Dean pack. Even though he's confident that they'll stay in touch, mostly because he trusts Dean to not let them drift apart, he is still sad knowing they'll never live together and be this involved in each other's lives again. He trusts he'll get over it, but he still dreads the empty feeling that he knows will come once Dean boards the bus to Stars Hollow for the last time and the city becomes that much lonelier. Dean insists that Jess walk him to the bus stop, so he does. As the bus is pulling up, Dean pulls Jess into a tight hug. Jess doesn't resist. Dean thanks him for everything and says he knows they'll see each other soon. Jess watches Dean board the bus, and he walks home alone. He makes it back to the quiet of his apartment before it hits him how alone he feels, how alone he has always felt in New York, and that he doesn't really have a good reason to stay.

Dean stays at Luke's in Stars Hollow while he gets his life in order. Luke has already moved in with Lorelai, but has left his furniture, his television and enough dishes and cookware that the place still feels like a home. Luke asks Dean to come down to the diner for dinner the first night he's there, on the house he says, and when Dean balks, Luke explains that no one who stays in his apartment pays to eat at the diner. Jess didn't. Lorelai didn't when she stayed over. He says he wants to talk about the apartment and tells Dean that he and Clara are welcome to stay there if they want, that there's no sense in paying to rent an apartment when they could use Luke's for free and save some money. That if Dean's interested, he'll get doors put up before Clara moves in. Tells Dean he inherited half of the building and paid cash for the rest, so there is no mortgage to cover. The utilities are connected to the diner, so Dean won't have to worry about those either. Only internet if he wants it, but if he does, he better not give the password to anyone other than Clara. He doesn't want his customers using the wi-fi in his diner. Dean tells Luke that sounds amazing and asks if he's sure. Luke is, but they are two stipulations Dean should know about before he says yes. The first is that Jess be allowed to stay on the couch if he wants to whenever he's in town. Dean stops Luke there, that of course, it's Jess' home. And, besides, Dean would let Jess stay with him anytime, anywhere. But, he balks at living there for free. He needs to pay rent. He had been planning on getting a one bedroom and sleeping on the couch. This would be so much better, having his own bed and his own space, but he won't feel right if he isn't paying Luke something to stay there. Luke smiles and tells Dean the second stipulation, that Dean go to college. Dean is thrown off, unsure what to say. Luke points out that Dean was planning on college before everything happened and if he's not paying rent there's no reason to not go now. Dean doesn't need to kill himself working multiple jobs to pay his bills. He can work one full time job and go to college part-time in the evening, take just one class at a time if that's what he wants. And on those nights when he has class, he won't need to worry about Clara. Luke will give her dinner in the diner and drive her to any tennis practice or friends' house or other activity that she needs to get to. That's the rent, that Dean study something and be working toward something more than Doose's while he lives there. Luke smirks and tells him that if he flunks out, Clara can stay, but he'll be out on his ass, just ask Jess. Dean laughs, accepts with a big grin and hugs Luke. Luke is reminded of how easy things are with Dean, how much he's going to enjoy having the kid around. And his heart hurts a little for Jess.

Dean accepts his old job back at Doose's. He's grateful to have it, grateful to Taylor for giving it to him, but everything feels worse this time around. It's not the pay, because he really doesn't need that much with no rent or utilities to cover. He hires Kirk to install internet access in the apartment and buys low-end cell phones for himself and Clara, and a refurbished laptop for school with some of his savings. But, other than that and day to day stuff like food and toiletries, his bills aren't that bad, and the job at Doose's covers them. It's more the boredom. He's been promoted from bag boy to register, but once he got the hang of running the register the new position became tedious very quickly. He isn't learning anything new or making himself more marketable. He was too late to apply for summer classes, but he works on his application for a couple of colleges in Hartford for the fall semester. He doesn't want to stagnate any longer than he needs to. Nicole was right to encourage him to pursue college and Luke was right to make him do it. This isn't enough.

After school lets out for the summer, Clara joins him in Stars Hollow. Their aunt drops her off with boxes of her stuff and though Dean tries to get her to stay the night and check out the town, offers her his bed, she declines, saying she needs to get back home. Dean knows she's sad about losing Clara, and he hopes she makes good on her promise to stay in their lives. She's the only family they have now aside from each other. That makes Dean think about his cousin. He asks his aunt for Kevin's address and writes him a long letter, apologizing for what he did with Millicent, explaining how messed up he was at that time but assuring his cousin that he knows that doesn't make what he did ok, stating that even though Kevin has a reason to hate him for life, he hopes he doesn't. He includes his new phone number. It feels like a lifetime ago that everything happened between them, but it still feels good to get the apology off his chest. He mails it out and hopes for the best. Two weeks later he gets a text from a number he doesn't recognize telling him that what's done is done and that he doesn't hate Dean. He wishes him and Clara well and says maybe they'll run into each other again sometime. They don't until Mel's funeral almost twenty years later, where they reconnect and meet each other's wives and children.

Jess has his call with the publishing house in Philadelphia. It's not as scary as he had anticipated. He speaks to a guy named Chris who would like to come out to New York to work with him in person for a few days if he can take some time off work, to get more of a feel for him and what his book is trying to say, and to go over ideas for some of the sections that he thinks could benefit from rewrites. He tells Jess that he always likes to do this face to face at the beginning, they can work over the phone and through email after that. Jess says he can take time off. He asks if he can come to them instead. He really needs to get out of the city for a while.

Jess puts everything he has into his book that summer, only taking a break from writing to spend fourth of July weekend in Stars Hollow at Luke's insistent prodding. Dean meets Jess' bus and greets him with a big hug as soon as he steps off. Jess is caught off guard, and jokes about not realizing they were people who hug now. Dean smiles at Jess' obvious discomfort, but doesn't apologize, explaining that hugging is what people do when they care about someone they don't get to see very often. So, it's the price Jess has to pay for living all the way over in New York. Jess, Dean and Clara have dinner at Luke and Lorelai's and then Jess goes home with Dean and Clara and crashes on the couch in the apartment. Rory's room still looks like Rory's room and it seems too weird to sleep in there. Luke understands.

The next time Jess goes back to Stars Hollow, he has something to report. He spends pretty much every minute of the summer that he isn't at Kinko's working on rewrites and having calls with his editor. He ends up with a published book and an offer to join their publishing company, as an editorial associate. Jess has regular calls with Luke and Dean but doesn't mention anything about his book until he goes back to Stars Hollow in the fall, with copies of his published novel for Luke and Dean, and an announcement that he's moving to Philadelphia. He debates asking Luke for Rory's address to hand deliver a copy to her as well. In the end he leaves the extra book with Luke and Lorelai to pass along to Rory. Luke and Dean both read the book over the next few weeks and call Jess to tell him how much they love it and how proud they are of him. They each tell him it's their favorite book. Jess smiles to himself during each of these conversations, realizing his instinct was right to not have bothered getting their opinions before he sent it to the publisher. He knows they love the book because they love him, and that's ok. Luke visits Jess in Philadelphia soon after he's settled in. He asks Jess to take him to the Philadelphia Museum of Art and when Jess is surprised at the request, Luke explains that he hasn't been to Philly since he was a kid on a school field trip and he's wanted to run up the Rocky steps ever since he watched the first movie, and he wants to do it now, while he still can. They do, and Luke makes it to the top first, a fact he enjoys bringing up for many years to come. Jess would be annoyed to get beat by someone twice his age, except that it makes Luke so happy. Jess vows to revamp his diet and start exercising so he can challenge Luke to a rematch.

Jess sees Rory from time to time in Stars Hollow, mostly at holidays and other family functions. He is always friendly, but keeps his distance, figuring he already put himself out there and got shot down. If they end up as anything more than pleasant acquaintances it will be because she wants them to be, not because he's forcing it on her. It's sometimes hard to not let old feelings resurface when he's around her, but he can usually manage to get through a family dinner in her presence without completely embarrassing himself. He quietly seethes when she dates a blond trust fund kid from Yale. From what Jess understands, the guy's family is so rich that they make the senior Gilmores look middle class. He hears some stories from Luke, who isn't crazy about the guy, then meets the guy for himself at Thanksgiving during Rory's senior year. Jess' first impression is that the guy's a dick. He doesn't get why Rory's with him when she could do so much better. The guy is obviously threatened by knowing that Rory used to date both Jess and Dean and he's slightly antagonistic toward them all through the meal, finding ways to subtly put them down while bragging about himself. Dean just smiles and laughs and lets everything go. Jess gets in a slightly heated exchange with the guy when Rory brings up his book and only stops when he finds himself on the receiving end of a very disapproving look from Luke. What bothers Jess most is how condescending this jerk is to Luke, explaining what he's studying at Yale and about his father's business as though speaking to a little kid. He's glad to see them break up some time later, until Rory visits him in Philadelphia for an event at the publishing house and attempts to make out with him as a kind of payback for the blond dick's cheating on her. She can't go through with it and runs out, sorry and embarrassed. Jess doesn't need to work as hard at controlling his feelings for her after that. It comes more naturally.

Dean is grateful to Lindsay for remaining friends with Clara. Lindsay is studying to be a teacher, and Dean can picture her being good at that. Lindsay takes Clara shopping for a dress for her first dance in junior high…and for her first bra…and her first feminine hygiene products. Dean is grateful for all of it. Lindsay's living at home while going to college and her mom invites Dean and Clara over for dinner every once in a while. At one dinner, when Lindsay's mom asks how work is going, he admits that he's burned out at Doose's, and wants to learn something new. Lindsay's dad says that Tom is looking for a new guy for his construction company, someone enthusiastic and trainable, he asks Dean if he'd like him to put in a good word for him. Dean says yes and thanks him, telling him how much he would appreciate that and promising to work really hard if Tom hires him. He starts working for Tom about a month later. Dean is continually humbled by how many people have been willing to help him in the past couple of years. He wants to pay it all back somehow. Or forward. Or something. He is still following Luke's rule and going to college part-time, and when he has to choose his major, he decides on criminal justice. The starting pay working for Tom isn't that much better than Doose's but Dean learns something new pretty much every day. He also enjoys the camaraderie of working with a group of guys. It reminds him of when he used to play basketball and hockey in high school. Between his new job, the night classes he's taking and Clara, he's starting to feel like his life is on the right track.

Living above the diner goes well. When Clara doesn't have tennis practice, debate club, or plans with a friend after school, she gets home before Dean gets out of work. He knows that at almost thirteen that she's old enough to stay home alone, but he still worries. He likes knowing that Luke is right downstairs if anything happens. He comes home many evenings to find Clara sitting at the counter in the diner, having a snack and doing her homework, or drinking a milkshake and telling Luke stories about her day. It's on one of those evenings as he's walking up behind Clara listening to Luke's earnest questioning in response to a story Clara was telling him, 'Are you serious, right in the middle of class, like that? That Trevor is just unbelievable! What did Sabrina do?' that Dean realizes that Luke has become family. He gets a little emotional and Clara asks why he's acting weird. Luke smiles and pats him on the shoulder and tells him to take a seat while he makes him something to eat.

Aunt Gretchen comes out every couple of months. Usually just a day trip, saying she doesn't want to impose. After one of her visits, Clara tells Dean how much happier she is back in Stars Hollow with him than she was with her aunt and uncle in New York. She loves him, and she knows he's given up stuff to take care of her, like getting to go to college full-time, and go out with girls and have friends his own age. She wants him to know how grateful she is, that she appreciates all of it. Dean is touched and gets a little choked up, he hugs her and says there is no place he'd rather be and nothing he'd rather do than be here with her. They spend the evening on the couch watching a movie, Dean content to be sitting there with his arm wrapped around the most important person in his life. Dean goes to sleep happy that night. Then wakes with a start at two o'clock in the morning at the realization that if anything happens to him, Clara would end up right back with Gretchen and Mel. He can't fall back to sleep and he ends up downstairs waiting for Luke when the man lets himself in to open the diner and jumps a mile at Dean's silhouette in the dark dining room. Dean tells him what he's worried about and says he needs to make a will, and that he wants Luke and Lorelai to be Clara's guardians if anything happens to him before she's eighteen. Luke brushes it off as anxiety. Tells Dean he is practically still a kid himself, young and healthy, nothing's going to happen to him. Dean says that's what his parents probably thought, too. Luke can tell he's serious. He agrees that he would take care of Clara if something were to happen to Dean. He'll talk to Lorelai, but he's sure she'll feel the same way. Luke talks to Lorelai that night and is surprised to hear her balk at the idea. She's happy to spend time with Clara and help them out when she can, but she's already raised her kid. She doesn't really want to sign on to raise someone else's. She tells Luke he doesn't understand what a huge commitment that is. Luke signs the paperwork himself anyway, knowing that if anything did happen to Dean, he would take Clara before letting her move back to New York to live with an abusive man. He has faith that if the situation were to arise, Lorelai would get on board with the idea. But, if she didn't, he supposes he would move back into the apartment with Clara until she turned eighteen. He doesn't mention this to Lorelai and she never brings up the topic again.

Jess gets over Rory and has a semblance of a romantic life in Philadelphia, where he occasionally has hook-ups, sometimes lasting one night and sometimes a few months. He doesn't bring anyone back to Stars Hollow and he doesn't meet any of their families either. It's never like that. When one of his co-workers asks for Jess' story one night when they're having beers, Jess is confused. Matthew tells him that he dates like a man who's had his heart torn out and ripped to shreds and is afraid to risk it happening again. He says there must be a good story there. This hits home for Jess. It's an accurate appraisal of his social life, but he doesn't have the story to go with it. He was the one who ran off on Rory. His heart got broken, but because of his own stupidity, not because a girl dumped him. He contemplates Matthew's comment, and realizes that his fear isn't of getting dumped, but of messing up with another girl he's in love with. He thinks about how it might have been easier to deal with if Rory had dumped him outright, and he didn't have himself to blame. He tells himself that what he did was years ago, and he vows to stop punishing himself for it. He's a different person now.

The next time Jess is at a family gathering, everyone brings a partner except him and Clara. Dean is with his new girlfriend. Jenny is Lindsay's cousin and after waiting long enough to make sure Dean was really over Rory, Lindsay had set them up. Dean introduces Jess as his best friend, and while this isn't news to Jess, he can admit he still likes hearing it. Rory brings home her boyfriend, Paul. Luke, Lorelai and Clara bombard the new additions to their holiday routine with questions. Clara's are mostly for Paul, because she already spends a lot of time with Jenny. Jess lets himself slide into observer mode. He likes both Jenny and Paul right away. They both seem genuinely nice. Jess feels like he already knows Jenny from all the stories he's heard from Dean. And, Paul is a relief to Jess after having met the blond dick from Yale. He's respectful to Luke and Lorelai, even when explaining the complicated technology he works with. He answers the questions they ask him and then gracefully turns the conversation to topics they know about, Stars Hollow activities, their businesses, and Rory's budding career in journalism. He even brings them thoughtful gifts. Before he leaves he makes a point of thanking Jess and Dean for being so welcoming to him. He hadn't known what to expect knowing that two of Rory's exes would be at her family's thanksgiving, and he appreciates how nice they've been to him. The earnestness of his comment would have won Jess over even if he didn't already like the guy. Over the next few years, Jess watches Rory neglect that relationship, sometimes to the point where he swears she forgets she even has a boyfriend, and it makes him think about the conversation with Dean on the bus back to New York where they were nineteen and Dean had told him how badly Rory had treated him when they dated. He recognizes that Rory isn't really interested in Paul and is just keeping him around as a space filler until she meets someone she has real feelings for. He thinks about how he would have found this realization hopeful a few years ago and would have told himself he still had a chance with her, but now he just finds is sad, and a little mean. When Paul finally ends things with Rory, Jess is sad to see him go, but relieved for Paul.

Jess also observes Dean and Jenny. He gets the inside scoop on that relationship from regular conversations with Dean. And he has to agree every time Dean says it, that yes, Jenny is really great. They seem balanced in the way he knows Dean was looking for. They are both very considerate of each other, and very much in love, sometimes to a sickening degree. Jenny does a lot with Clara and between Jenny, Lindsay and sometimes Lorelai, he knows Dean feels like he has the female role model stuff covered for Clara. When they start getting serious, Luke tells Dean that Jenny is welcome to move in with him if that's what he wants. He would be ok with that and it wouldn't change their rent situation or anything. Jenny moves in the following month and they stay in the apartment for a few years, until Dean has finished college and Clara is just starting. When Jess comes home that spring, he can see Dean, Jenny and Clara as their own little family in the making. When Dean takes him to watch Clara's tennis match, they sit together in the bleachers, while Lindsay and Jenny stand together courtside moving back and forth between all the girls' matches carrying supplies, it being Jenny's turn to play 'team mom' and bring the girls snacks and drinks in between sets and deal with any first aid situations that come up. When Dean explains to Jess that he offered to sign up for the role himself, but Clara had shot him down by saying it was 'team mom' not 'team Dean' meaning it's supposed to be a girl, Jess' heart goes out to Clara remembering all the times in his own childhood when he had tried to claim one of Liz's better boyfriends or husbands for himself. He watches the huge grin on Clara's face as she high-fives Jenny and Lindsay after finishing her first set and he hopes things work out better for her than they did for him. And Jess is pretty sure they have when he's at Dean's wedding a couple of years later. Jess is the best man and Clara and Lindsay share the maid of honor duties. But, it's when Jess is a guest at Clara's wedding about fifteen years after that, and he sees Jenny at the altar as Clara's maid of honor, that he knows for sure.

Jess and Lorelai's relationship vacillates between awkward and mildly pleasant with the occasional bit of tension thrown in for the rest of their lives. Luke and Lorelai get married after dating for almost ten years. Jess makes a point of asking Lorelai to dance at the reception, and Lorelai jokes about being his 'wicked step mother.' Jess smiles and appreciates what the comment says about his relationship with Luke. They never become as close as Luke and Rory, but they try, and they at least succeed at significantly lowering their mutual annoyance and animosity. They come to what Jess can only describe as a grudging respect for each other. They both love Luke and they are both willing to endure each other with a smile in order to make him happy. The hug each other whenever Jess arrives at their house, and Lorelai sometimes accompanies Luke into Philadelphia to visit Jess. And Jess can admit that when Lorelai isn't targeting him with passive aggressiveness, she can be funny, and maybe even enjoyable to be around. But, there remains no real emotional connection between them. They don't exchange 'I love you's until almost twenty-five years after the wedding, bereft and heartbroken in the hallway of the hospital after saying goodbye to Luke for the last time. Rory and her daughter are on a plane back from London that doesn't arrive in time, Dean and Jenny are visiting their son at college in New Hampshire, and Clara is at a conference in Chicago. Jess feels it's fitting that he and Lorelai are the only two there in Luke's final moments. Lorelai grabs him unexpectedly as they're leaving, tells him how much he meant to Luke, that Luke loved him like a son, and was so proud of him, that he was a such a good son to Luke, the best he could have asked for. She tells him that she loves him, too, and not to be a stranger. All he can really get out is a quiet 'you, too.' He debates driving back to his empty apartment in Philly, but it's late and he knows Luke would want him to stay and help Lorelai with the arrangements for the funeral so he spends the night alone in the apartment over the diner, under the guise of leaving the extra bed at Lorelai's for Rory, but really just needing to be alone.

He ends up helping out in the diner for a few days to keep busy. Caesar pretty much runs the place now and he fills Jess in on how he had walked out of the kitchen one night after closing to find Luke clutching his chest and having trouble breathing. To everyone's knowledge, Luke had been in good health even in his seventies and the heart attack had been a shock. Lorelai shows Jess a copy of the will and he learns that Luke left all his investments and liquid assets to Lorelai, but the diner and apartment to Jess, with the explanation that he wanted Jess to always feel that he had a home there. Jess chokes up at that, knowing that any connotation to home Stars Hollow held for him was tied to the man he just lost, not the apartment he had once lived in. But, he stays on anyway, not quite ready to face his life yet, going over the books and paperwork and learning about the business from Caesar, and spending his evenings with Dean and Jenny, or with Lorelai, or by himself reading or thinking. His first decision as owner is to give Caesar a big raise, partly because the guy has a lot more responsibility now with Luke gone and partly to thank him for having been loyal to Luke all these years. When he feels like he's used up all the acceptable bereavement time he can, he calls Chris at work to say he's taking a leave of absence from the company. He needs to focus on his own writing for a while. He feels empty. He has nothing to offer other writers right now.

He ends up spending the next year and a half in Stars Hollow, writing whenever he's not helping out at the diner or spending time with Dean or Lorelai. He also has a minor mid-life crisis. He thinks about how little he has in his life for how far along it is, more than half over. He never found anyone he wanted to share his life with. His longest relationship had lasted for four years in his late twenties to early thirties. He and Sarah had even shared an apartment for two of those years, but she had ended things when she had started wanting to have a baby and he hadn't. He knew he had loved her, and it had hurt to lose her, but a small, scared part of him had felt relieved to return to his comfort zone of being alone, where he didn't need to worry about how his behavior would impact someone else. He had spent the next twenty years avoiding serious romantic entanglements. Now that he's older, he sometimes regrets not having had a child with her when he had the chance, not having tried harder with Sarah in general. He hadn't trusted himself with the idea of being a parent, but now that the chance is past, his apprehension doesn't feel like a very worthwhile reason to have missed out on something so significant in life. Jess has a few good friends, but the older he gets the less that feels like enough. And now, with Luke gone, his life feels that much smaller and lonelier. He honestly enjoys his work most days, which he knows is more than a lot of people can say, enjoys helping other writers work through their stories, but there's only so much personal fulfillment he can get from helping other writers with their books, their words. When he looks back at three decades of that, he isn't sure it's enough to make his life feel well lived. The only book he ever had published was his first. He has started several other projects over the years, but none felt right, so he never finished them.

He sees Stars Hollow differently this time around, not as the hell he had felt stuck in at seventeen, but as the place that had been the only home Luke have ever known. He tries to think about his uncle's life from his point of view. Vignettes start crafting themselves in his mind. He starts to see a novel, an homage to the person who loved him more than anyone else ever has or likely ever will, the man who saved his life, for whatever his life may be worth. The scene where Luke greets his belligerent nephew at the bus stop. Or breaks through the wall with a sledge hammer. Or takes him out in a boat after a vicious swan attacks him. The terrible, horrible fight the night Luke tells him he has to go. The teary middle of the night reconciliation weeks later. But, then he realizes that that's where his story with Luke started. But, maybe this story needs to start earlier. He considers Luke's childhood, but decides to include the relevant information about his family by weaving it into the current day story line, instead of starting there and going through an entire life story. He thinks about the big moments in Luke's life. About how Luke would start his own story if he were the one writing it. And Jess can see it. The diner. A physical longing. And a pretty brunette begging for a coffee fix.

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Jess gave the manuscript to Dean, wanting a second opinion before bringing it to his partners at the publishing house, feeling that he was too close to the subject matter himself to be at all objective about the quality of the writing. The following week found Jess sitting on Dean's porch swing nursing a beer. He had come over for dinner but hadn't wanted to bring up the book until they were alone. Jenny had gone to bed and the two foster children currently placed with them were playing video games in one of the upstairs bedrooms. Jess could hear the occasional groan or excited shriek float down from the open window. Dean and Jenny had seen Clara through her teenaged years and raised a son and daughter of their own. When their youngest had gone off to college a few years ago, Jess had expected them to savor being alone for the first time in their relationship. Instead, they had started taking in foster children. Jess blamed Clara, who worked as a social worker in Hartford, for constantly talking about the shortage of foster homes in Connecticut and finally convincing Jenny they should foster by telling her that anyone who was as capable of making a motherless child feel as loved as she had made Clara feel when she was a teenager should be a foster parent. According to Dean, his knew his fate was sealed when Jenny had teared up and hugged Clara.

"So, let me have it. What do you think?" Jess took a sip of his beer. "But, two rules. Be completely honest, and no hugging."

Dean grinned, laid back casually in his chair, pressing his foot against the bottom of the one Jess had crossed over his leg, jostling the swing slightly. "C'mon, man. You know I can't make any promises on the second one. These things can't be planned. I'm a spontaneous hugger. It's part of my charm." It was still weird to Jess that someone as warm and affectionate as Dean worked as a detective in Hartford. Dean joining the police force had made Jess rethink his whole perspective on cops.

"Hmm…..self-reporting your charm. That's always credible."

"What do I think? I think you're still an ass, that's what I think." Jess barked out a laugh at that. "Oh, sorry, did you mean about the book?"

Jess nodded. "Yeah, give it to me."

"I loved it, Jess. So much. It's my new favorite book."

"That would mean a lot more to me if you'd read more than ten books in your whole life, or if you had a past history of decent taste in books, which you do not." Jess' sarcasm still came up around Dean, as it always had with Luke too, but they both knew nothing was meant by it. Dean understood, as had Luke, that most of Jess' sarcasm was just a way that felt safe for him to connect with the people he cared about and was rarely ever about the meaning of the words themselves.

"I'm serious. I thought it was great. It was truthful enough that I could see who the characters were based on, but different enough that I didn't always know where things were leading in the short term. Although, of course, I always knew how it would end."

"If it wasn't based on people you knew or cared about, would you still have been interested in the story?"

"Absolutely! it's everything I like. Hokey little small-town setting. Quirky characters. I love 'Mick' by the way. He's even more Kirk-like than Kirk, if that's possible. Like, I picture Kirk reading this book and getting pissed that he never thought of some of the things that Mick does. It made me smile whenever that guy showed up. And the gossipy older ladies were a riot! All I can say is you're lucky Babette isn't still alive to sue your ass. Cause she totally would! Remember how much she hated you after you swiped her gnome?"

Jess nodded, a small smile on his face. "I remember."

"And thanks for not using anything about me being homeless. Not that I'm ashamed of it or anything, I just….I don't know. Didn't want people reading about it, I guess." Dean trailed off.

"I would never have included any of that stuff without talking to you." Jess was serious now. "I hope you know that. All the stuff in New York. That's personal. I feel like that's our story. It's not anyone else's business." Jess stopped to think about that. It was their story. And there was good stuff there.

"I appreciate that. Really."

"Of course, Dean. So, what else did you think?"

"I loved the main relationship Jess. You captured Luke so well. You made him different enough to be a fictional character, but it was still so _him_. Your character, too. You did an amazing job of depicting what a little shit you used to be and how crazy you must have driven Luke. That couldn't have been easy."

Jess paused for a minute at Dean's perspective on the main relationship of the story. Even though both story lines had gotten pretty much equal coverage, he had assumed readers would see the relationship between the Luke and Lorelai inspired characters as the main event. "Yeah? Thanks. And it wasn't easy, but it wasn't as hard as I expected either to get myself back in that headspace. I may act more together and mature on the outside, but sometimes I feel like that 'little shit' as you put it still lives it my head. I just stopped voicing his thoughts for the most part."

Dean laughed and took a drink from his bottle. "And, the parts about your parents were so good. I had expected to see them portrayed as the bad guys, you know, after hearing the way you always talked about them, especially your dad. But, you did a really good job of humanizing them. I felt bad that your character had to deal with them, but I didn't out and out hate them, or anything. Even though I expected to. I almost felt sorry for them."

"Was there anything you didn't like about it?" Jess knew Dean would support anything he did, he was that kind of friend, but he knew he had to have noticed flaws, too.

Dean started shaking his head before Jess had finished the question. "Nope. I know you're not going to believe me, but there wasn't. I liked the whole thing. I want a real copy when it's published, so I can read it again."

Jess was giving Dean a reproachful look, not believing there wasn't a part that Dean thought needed improvement. Maybe Dean was too close to the subject matter, too. Or maybe, like Luke always had, Dean still made a better support system than a book critic.

As if reading his mind, Dean said. "And if Luke were here to read this, Jess, I know he would agree with me. He would have loved this book. He was always so proud of you and he would have been so touched by this. You know that, right?"

Jess nodded silently, not sure what to say, wishing he had done something like this while Luke was still around to appreciate it. What came out surprised him. "I miss him so much."

"I miss him, too." Dean got up from his chair and moved to sit beside Jess on the porch swing.

Jess felt the swing sway slightly as Dean sat down and wrapped an arm around his shoulders. "I see you're still taking any display of emotion as an invitation to grope me, huh?"

Dean squeezed Jess' shoulder. "It's only fair. You're still using sarcastic barbs to distract from your emotions. And, you know how I operate. If you don't want to get groped, don't look like you need a hug in my immediate vicinity." Dean's voice turned softer, more serious. "I get it, though. I still miss my parents pretty much every day.

"Yeah?"

"Yeah. I've spent my whole life missing them. Whenever anything happens, good or bad, that I wish they were here for. Can I give you some advice, Jess?"

"Could I really stop you?"

Dean ignored him. "I'm going to quote my favorite author and tell you that even though Luke's gone, he's still with you in all the ways that matter. He did right by you when no one else would, and all the stuff that was good about him rubbed off on you in how much he loved you and became a part of you. You still have him with you and you always will."

Jess stared straight ahead into the dark. "I don't know who your favorite author is, but that isn't from my book."

"No, it's not. It's what you told me one night in New York, when I was lying on your floor, getting choked up talking about my parents. I always remembered it because it was of the few things anyone said to me back then that actually made me feel even a little bit better."

"I told you that your parents 'did right by you when no one else would'? That was my great advice? That doesn't even make sense. Plus, it sounds way too folksy for me."

"I may have paraphrased to fit the situation. But, the meaning is still there. Luke will live on in you the same way my parents live on in me and Clara. And, this book is proof of that. It's this amazing love letter to the person that you feel saved you. And I get it, because if I was a writer, I'd write a book about how you saved me in New York."

"Oh, c'mon, it's totally different. I didn't save you. Not the way Luke did with me. You were just in a bad place at the time, but you would have gotten out of it one way or another, even if I hadn't found you."

Dean removed his arm from Jess' shoulder and turned in his seat to face him. "Look at me, Jess." Jess sighed softly and repositioned himself on the swing so that he was facing Dean. "I was at the end of my rope that night in the alley. I was done. It was over for me. I felt hopeless, worthless. I had no place to go, and no one to be with, and I couldn't take it anymore. I was ready to sit down on that cardboard box and go to sleep and never wake up. I had given up."

Dean took in Jess' look of disbelief. "Yeah, don't believe me? Ask anyone who was in the Hartford public school system in the past twenty years."

"What does that even mean?"

"I'm not a writer, Jess. I could never do anything for you like what you did for Luke with this book. But every year, they send a few cops to the schools to talk to the kids about different things, bullying, drugs, that kind of stuff. My topic is always suicide prevention. Because I do it so well. I go over suicide statistics for teenagers, I tell them what they should do and who they should call if they're experiencing suicidal ideation, and lastly, I leave them with my story, our story, from that night in the alley in New York to really drive home the point that even when it doesn't seem like it, things can get better, and that they should always be nice to each other because you never know when one act of kindness will be the thing that changes someone's life."

Jess stared at Dean, shocked into speechlessness, but maintaining eye contact. He was grateful when Dean spoke again, his tone lighter. "And, I'm a police officer, so you know I can't lie."

Dean smirked, and Jess huffed out a laugh. "Yeah, right."

"Ok, how about I've been your best friend for over thirty years, I'm practically the brother you never had, so you know I _don't_ lie."

Jess nodded. "I believe you. And, all I can say is, if that's how it was for you that night in the alley, then I'm glad I was there, because bringing you home with me that night was easily the best thing I've done with my life."

Dean leaned forward on the swing, closing the space between them. Jess met him halfway and hugged back, reflecting on having been cast as the hero in Dean's story the same way he had cast Luke as the hero in his. He wasn't sure what he had done for Dean could measure up to what Luke had done for him, but he knew Dean was right about one thing: you never know when one act of kindness will change someone's life. He had come over tonight to get validation for his novel, but what he got instead was even better.

***The End***


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